DE19536730A1 - 2-hydroxyphenyltriazines - Google Patents

Abstract

The invention relates to novel 2-hydroxyphenyltriazines and to homopolymers and copolymers obtainable therefrom, as described in greater detail in claims 1 and 5; the novel compounds can be used as UV absorbers in or for organic materials.

Description

The present invention relates to novel 2-hydroxyphenyltriazines, a process for theirs Preparation and its use as a UV absorber in organic materials.

EP-A-0 434 608 discloses hydroxyphenyltriazine-type UV absorbers, especially in Combination with sterically hindered amines known. Further connections this In US-A-5,189,084, EP-A-530,135, US-A-5,364,749 and US Pat US-A-5,300,414.

UV absorber of the hydroxyphenyltriazine type in, for example, is also known To use paints. In US 3,423,360 are polymeric Hydroxyphenyltriazinacrylate or methacrylates described and documented their use in paints.

However, the known UV absorbers often have undesirable properties such as for example: insufficient inherent stability to light, heat or moisture, Migration or volatility, difficult emulsification, formation of crystals, or too Clumping.

We have now found a group of 2-hydroxyphenyltriazine UV absorbers which Surprisingly, the demands made by the technology to a great extent fulfill.

Also, combinations of the 2-hydroxyphenyltriazines according to the invention with others Types of UV absorbers such as benzophenones, benzotriazoles, sterically hindered Amines, oxanilides, cyanoacrylates, salicylic acid esters, acrylonitriles or thiazolines are suitable for the stabilization of organic materials.

The subject of the present application are thus 2-hydroxyphenyltriazines of the formula I.

wherein the radicals
E₁ and E₂, independently of one another, represent a group of the formula Ia or Ib

and wherein A is -C (= O) -CR₅ = CH-R₆;

-CH₂-C (= CH₂) -R₁₀,
- (CH₂) _p -SiR₁₁R₁₁'-CH = CH₂, -C (= O) - (CH₂) _q -CH = CH₂, or
-C (= O) -O-CH₂-C (= CH₂) -R₁₀; and,
in the case that R₃ 'has the meaning -O-CR₈R₈' - (CH₂) ₁-XA, R₁ additionally has the meanings C₁-C₁₈-alkyl and C₃-C₂₀-alkyl, which is represented by -O-, -CO-O- or - O-CO- is interrupted, including; such as
in the case that E₁ is a group of the formula Ia in which none of the radicals R₂ and R₁₄ is hydrogen, R₁ additionally the meanings -A, -CH₂-CH (XA) -CH₂-O-R₇, -CR₈R'₈- (CH₂ ) ₁-XA, -CH₂-CH (OA) -R₉, -CH₂-CH (OH) -CH₂-XA, -CHR₈- (CH₂) _r -C (= O) -O-CH₂-CH (OH) - CH₂-OA and -CR₈R'₈- (CH₂) ₁-C (= O) -XA; such as
in case E₁ is a group of formula Ib, R₁ additionally includes -CH₂-CH (XA) -CH₂-O-R₇;
R₂, independently of one another, is H, C₁-C₁₂-alkyl, cyclohexyl, C₃-C₆-alkenyl, halogen, phenyl or trifluoromethyl;
R₂ ', independently, C₁-C₁₈ alkoxy, C₃-C₁₈ alkenoxy, -OH or -O-CO-R₁₂;
R₃ and R₃ 'are independently H, -OH, -O-CH₂-CH (XA) -CH₂-O-R₇,

-O-CH₂-C (= CH₂) -R₁₀,
-O- (CH₂) _p -SiR₁₁R₁₁'-CH = CH₂, -OC (= O) - (CH₂) _p -CH = CH₂, -OC (= O) -O-CH₂-C (= CH₂) -R₁₀, -O-CR₈R₈ '- (CH₂) ₁-XA, -O-CH₂-CH (OA) -R₉, -O-CH₂-CH (OH) -CH₂-XA, -O-CHR₈' (CH₂) _r -C (= O) -O-CH₂-CH (OH) -CH₂-OA, -CR₈R'₈- (CH₂) ₁-C (= O) -XA, C₁-C₁₈-alkyl, C₆-C₁₂-cycloalkyl, C₃- C₁₈-alkenyl, -OR₁₃₁, halogen, trifluoromethyl, phenyl, phenyl-C₁-C₄-alkyl, -CN, C₁-C₁₈-alkyl-S (= O) _t - or phenyl-S (= O) _t -; R₄, R₄ 'and R₄'', independently of one another, H, C₁-C₁₈-alkyl, C₃-C₆-alkenyl, -OR₁₃₁, halogen, trifluoromethyl, phenyl, phenyl-C₁-C₄-alkyl, having one to three radicals C₁- C₄-alkyl-substituted phenyl-C₁-C₄-alkyl, -CN, C₁-C₁₈-alkyl-S (= O) _t or phenyl-S (= O) _t -;
R₅ is H, -CH₂-COOR₁₃, C₁-C₄-alkyl or -CN;
R₆ is H, -COOR₁₃, C₁-C₁₇-alkyl or phenyl;
R₇ is C₁-C₁₈ alkyl; C₅-C₁₂ cycloalkyl; C₃-C₁₅ alkenyl; phenyl; with one to three radicals C₁-C₈-alkyl, C₁-C₈-alkoxy, C₃-C₈-alkenoxy, halogen or trifluoromethyl-substituted phenyl; Phenyl-C₁-C₄-alkyl; interrupted by one or more -O- interrupted C₃-C₅₀-alkyl; 1-adamantyl; 2-adamantyl; norbornyl; Norbornane-2-methyl; or -C (= O) -R₁₂;
R₈ and R ₈ ', independently of one another, H or C₁-C₁₈-alkyl, phenyl, phenyl-C₁-C₈-alkyl, or having 1 to 3 radicals C₁-C₄-alkyl, C₃-C₈-alkenoxy, C₁-C₈-alkoxy , Halogen, CF₃ substituted phenyl;
R₉ is C₁-C₁₈ alkyl, phenyl or phenyl-C₁-C₄ alkyl;
R₁₀ is H or -CH₃;
R₁₁ and R₁₁ 'are independently C₁-C₄ alkyl or phenyl or phenyl substituted with one to three C₁-C₈ alkyl, C₁-C₈ alkoxy, C₃-C₈ alkenoxy, halogen or trifluoromethyl; R₁₂ H, C₁-C₁₈ alkyl, C₂-C₁₅ alkenyl, phenyl, phenyl-C₁-C₄-alkyl, C₅-C₁₂-cycloalkyl, C₁-C₁₂ alkoxy, phenoxy, norbornan-2-yl, 5-norbornene-2 -yl, 1-adamantyl; R₁₃ is H, C₁-C₁₈ alkyl, C₃-C₁₅ alkenyl, phenyl, C₅-C₁₂ cycloalkyl, C₃-C₅₀ alkyl interrupted by one or more -O-; with one to three radicals C₁-C₈-alkyl, C₁-C₈-alkoxy, C₃-C₈-alkenoxy, halogen or trifluoromethyl-substituted phenyl, phenyl-C₁-C₄-alkyl, 1-adamantyl, 2-adamantyl, norbornyl, norbornane-2 -methyl;
R₁₄ and R₁₅, independently of one another, H, C₁-C₁₈-alkyl, C₃-C₁₈-alkenyl, C₆-C₁₂-cycloalkyl, halogen, CF₃, phenyl, phenyl-C₁-C₄-alkyl, CN, C₁-C₁₈-alkyl-S (= O) _t - or phenyl-S (= O) _t - or -OR₁₃₁;
R₁₃₁ C₁-C₁₈ alkyl; C₃-C₁₈ alkenyl; C₁-C₁₈-alkyl which is substituted by OH, C₁-C₁₈-alkoxy, C₅-C₁₂-cycloalkoxy, C₃-C₆-alkenyloxy, halogen, -COOR₁₃, -CONH₂, -COHNR₁₃₂, -CON (R₁₃₂) (R₁₃₃), -NHCOR₁₂, CN, -OCOR₁₂, phenoxy, and / or by C₁-C₁₈-alkyl, C₁-C₁₈-alkoxy or halogen-substituted phenoxy; C₃-C₁₈ alkenyl;
C₆-C₁₂ cycloalkyl; C₆-C₁₂-cycloalkyl substituted by C₁-C₄alkyl and / or -OCOR₁₂; interrupted by one or more -O- interrupted C₃-C₅₀-alkyl which is unsubstituted or substituted by OH or O-CO-R₁₂; phenyl; Phenyl-C₁-C₄-alkyl;
-COR₁₂; -SO₂R₁₂;
R ₁₃₂ and R₁₃₃, independently, C₁-C₁₂ alkyl, C₃-C₁₂ alkoxyalkyl, C₄-C₁₆ dialkylaminoalkyl, C₁-C₁₂ cycloalkyl; or
R₁₃₂ and R₁₃₃ together C₃-C₉-alkylene, C₃-C₉-oxaalkylene or -Azaalkylen;
X is -NR₈-, -O-, NH- (C _n H _2n ) -NH or O- (C _k H _2k ) -NH-;
k is a number 2-4;
l is a number 0-19;
m is a number 2-8;
n is a number 0-4;
p is a number 0-10;
q is a number 1-8;
r is a number 0-18; and
t is a number 0, 1 or 2.

Substituents in the formula (I) are alkyl having up to 18 carbon atoms, so radicals such as methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, Nonyl, decyl, undecyl, dodecyl, tetradecyl, hexadecyl or octadecyl and corre branched isomers in question.

Substituents in the formula (I) are alkoxy having up to 18 carbon atoms, so For this purpose, radicals such as methoxy or ethoxy and the above-mentioned alkyl radicals analogues Remains in question.

Substituents in the formula (I) are alkenyl having up to 18 carbon atoms, so For this purpose, radicals such as vinyl, prop-1-enyl (-CH = CH-CH₃) or prop-2-enyl (-CH₂-CH = CH₂) and the above alkyl radicals analogous radicals in question.

Substituents in the formula (I) are alkenoxy having up to 18 carbon atoms, so  For this purpose, radicals such as prop-1-enoxy (-O-CH = CH-CH₃) or prop-2-enoxy (-O-CH₂-CH = CH₂) and the above alkyl radicals analogous radicals in question.

Substituents in the formula (I) phenyl-C₁-C₄-alkyl or having one to three radicals C₁-C₄-alkyl-substituted phenyl-C₁-C₄-alkyl, so here are radicals such as

in question.

Substituents in the formula (I) phenyl-C₁-C₄-alkoxy, so come for this radicals as

in question.

If substituents in the formula (I) are halogen, this is fluorine, chlorine, bromine or iodine in question.

Preferably, R₁ is -CH₂-CH (OA) -CH₂-O-R₇ or

Preferably, R₂ is H, C₁-C₄ alkyl, C₃ alkenyl, F, Cl or phenyl; especially preferably H, -CH₃ or Cl; and most preferably H or -CH₃.

Preferably, R₂ 'is -OH, C₁-C₄-alkoxy, C₃-alkenoxy; especially preferred -OH, C₁-C₂-alkoxy, C₃-alkenoxy; and most preferably -OH.

Preferably, R₃ or R₃ represents -O-CH₂-CH (OA) -CH₂-O-R₇,

-O-CR₈R₈ '- (CH₂) ₁-OA, -O-CH₂-CH (OA) -R₉
-O-CH₂-CH (OH) -CH₂-XA, H, -OH, C₁-C₄-alkyl, cyclohexyl, C₃-alkenyl, C₁-C₄-alkoxy, C₃-alkenoxy, F, Cl, trifluoromethyl, phenyl, phenyloxy , Benzyl, benzyloxy or -CN; particularly preferably H, -OH, -O-CH₂-CH (OA) -CH₂-O-R₇,

-O-CH₂- (CH₂) ₁-OA, -CH₃,
C₁-C₄ alkoxy, C₃-alkenoxy, F, Cl, phenyl, benzyloxy or -CN; and very particularly preferably H, -OH, -O-CH₂-CH (OA) -CH₂-O-R₇,

-O-CH₂- (CH₂) ₁-OA, -CH₃, -OCH₃, Cl, phenyl or -CN.

Preferably, R₄, R₄ 'or R₄' 'is H, C₁-C₄alkyl, C₃-alkenyl, C₁-C₄alkoxy, C₃-alkenoxy, F, Cl, trifluoromethyl, phenyl, phenyl-C₁-C₃-alkyl or -CN; especially preferably H, -CH₃, C₃-alkenyl, -OCH₃, C₃-alkenoxy, F, Cl, phenyl-C₃-alkyl or -CN; and most preferably H or -CH₃.

Preferably, R₅ is H or -CH₃.

Preferably, R₆ is H, -COOR₁₃, -CH₃ or phenyl; and particularly preferably H or -CH₃.

Preferably, R₇ is C₁-C₈ alkyl, cyclohexyl, C₃-C₈ alkenyl, phenyl, with one to three C₁-C₄ alkyl or C₁-C₄ alkoxy radicals substituted phenyl or benzyl; and especially preferably C₁-C₅-alkyl, cyclohexyl, C₃-alkenyl, phenyl or benzyl.

R₈ and R₈ 'are preferably independently of one another, H or C₁-C₈-alkyl.

R₁₀ is preferably hydrogen.  

R₁₁ and R₁₁ 'are, independently of each other, preferably C₁-C₄ alkyl or phenyl, before all methyl.

X is preferably -O- or -NR₈-, especially an oxygen atom.

The value of the index 1 is preferably 1-15.

Compounds of the formula I which can be used according to the invention therefore correspond, for example example of the formula Ic

wherein the radicals
A is -C (= O) -CR₅ = CH-R₆;
R₁, independently of one another,

-CH₂-C (= CH₂) -R₁₀, - (CH₂) _p -SiR₁₁R₁₁'-CH = CH₂, -C (= O) - (CH₂) _q -CH = CH₂, or -C (= O) -O- CH₂-C (= CH₂) -R₁₀; and,
in case R₂ 'is OH or OA, R₁ additionally comprises -CH₂-CH (OA) -CH₂-O-R₇;
R₂ and R₂ 'are independently H, -OH, -OA, C₁-C₁₂ alkyl, cyclohexyl, C₃-C₆ alkenyl, C₁-C₁₈ alkoxy, C₂-C₁₈ alkenoxy, halogen, phenyl or trifluoromethyl;
R₃ and R₃ 'are independently H, -OH, -OA, the above-mentioned -OR₁, -O-CHR₈- (CH₂) ₁-OA, -O-CH₂-CH (OA) -R₉, -O-CH₂ -CH (OH) -CH₂-OA, O-CHR₈- (CH₂) _r -C (= O) -O-CH₂-CH (OH) -CH₂-OA, C₁-C₁₂-alkyl, cyclohexyl, C₃-C₆- Alkenyl, C₁-C₁₈-alkoxy, C₃-C₁₈-alkenoxy, halogen, trifluoromethyl, phenyl, phenyloxy, phenyl-C₁-C₄-alkyl, phenyl-C₁-C₄-alkoxy, -CN, C₁-C₁₅-alkyl-S (= O) _t - or phenyl-S (= O) _t -;
R₄, R₄ 'and R₄'', independently of one another, H, C₁-C₁₂-alkyl, C₃-C₆-alkenyl, C₁-C₁₈-alkoxy, C₃-C₁₈-alkenoxy, halogen, trifluoromethyl, phenyl, phenyloxy, phenyl-C₁- C₄-alkyl, phenyl-C₁-C₄-alkyl substituted with one to three radicals C₁-C₄-alkyl, phenyl-C₁-C₄-alkoxy, -CN, C₁-C₁₈-alkyl-S (= O) _t - or phenyl- S (= O) _t -;
R₅ is H, -CH₂-COOR₁₃, C₁-C₄-alkyl or -CN;
R₆ is H, -COOR₁₃, C₁-C₁₇-alkyl or phenyl;
R₇ is C₁-C₁₈-alkyl, cyclohexyl, C₃-C₁₈-alkenyl, phenyl, with one to three radicals C₁-C₈-alkyl, C₁-C₈-alkoxy, C₂-C₈-alkenoxy, halogen or trifluoromethyl-substituted phenyl, phenyl-C₁- C₄-alkyl, or -C (= O) -R₁₂;
R₈ is H or C₁-C₁₈ alkyl;
R₉ is C₁-C₁₈ alkyl, phenyl or phenyl-C₁-C₄ alkyl;
R₁₀ is H or -CH₃;
R₁₁ and R₁₁ 'are independently C₁-C₄ alkyl or phenyl or phenyl substituted with one to three C₁-C₈ alkyl, C₁-C₈ alkoxy, C₃-C₈ alkenoxy, halogen or trifluoromethyl;
R₁₂ is C₁-C₁₈ alkyl, C₂-C₁₈ alkenyl or phenyl;
R₁₃ is H, C₁-C₁₈ alkyl, C₃-C₁₈ alkenyl or phenyl;
l is a number 0-19;
p is a number 0-10;
q is a number 1-8;
r is a number 0-18; and
t is a number 0, 1 or 2.

Preference is given to compounds of the formula (I) in which the radicals R₂ are H, C₁-C₄-alkyl, C₃-alkenyl, F, Cl or phenyl;
R₂ is C₁-C₄ alkoxy, C₃-alkenoxy, -O-CO-R₁₂ or -OH;
R₃ and R₃ 'are independently H, -OH, -O-CH₂-CH (XA) -CH₂-O-R₇,

-O-CHR₈- (CH₂) ₁-XA,
-O-CH₂-CH (OA) -R₉, -O-CH₂-CH (OH) -CH₂-XA, C₁-C₄-alkyl, cyclohexyl, C₃-alkenyl,
-OR₁₃₁, F, Cl, trifluoromethyl, phenyl, benzyl or -CN;
R₄ 'and R₄'', independently of one another, H, C₁-C₄-alkyl, C₃-alkenyl, C₁-C₄-alkoxy, C₃-alkenoxy, F, Cl, trifluoromethyl, phenyl, phenyl-C₁-C₃-alkyl or -CN ;
R₅ is H or -CH₃;
R₆ is H, -COOR₁₃, -CH₃ or phenyl;
R₇ C₁-C₈-alkyl, cyclohexyl, C₃-C₈-alkenyl, phenyl, having one to three radicals C₁-C₄-alkyl
or C₁-C₄-alkoxy-substituted phenyl or benzyl;
R₉ is C₁-C₁₀ alkyl, phenyl or benzyl;
R₁₁ and R₁₁ ', independently of one another, C₁-C₄-alkyl or phenyl;
R₁₂ is H, C₁-C₁₈-alkyl, C₂-C₃-alkenyl, phenyl, phenyl-C₁-C₄-alkyl or cyclohexyl;
R₁₃ is C₁-C₄alkyl, C₃-alkenyl, cyclohexyl, phenyl-C₁-C₄alkyl or phenyl;
R₄, R₁₄ and R₁₅, independently of one another, H, C₁-C₈-alkyl, F, Cl, C₁-C₄-alkoxy, CF₃,
Phenyl, or CN;
R _{131 is} C₁-C₁₈ alkyl; C₃-C₁₈ alkyl which is substituted by OH, C₁-C₁₈ alkoxy,
C₅-C₁₂-cycloalkoxy, -COOR₁₃, -CONH₂, -COHNR₁₃₂, -CON (R₁₃₂) (R₁₃₃), -NHCOR₁₂, CN, -OCOR₁₂ and / or phenoxy; C₃ alkenyl; C₆-C₁₂ cycloalkyl; interrupted by one or more -O- interrupted C₃-C₅₀-alkyl which is unsubstituted or substituted by OH or OCOR₁₂; phenyl; Phenyl-C₁-C₄-alkyl; -COR₁₂; -SO₂R₁₂;
X is -O- or -NR₈-;
l is a number 1-19; and
pure number 0-10 mean.

Particularly preferred are compounds of the formula (I) in which E₁ and E₂, independently of one another, represent a group of the formula Ia or Ib and in which

means, and in the case that R₃ '
-O-CR₈R₈ '- (CH₂) ₁-XA, R₁ additionally has the meanings C₁-C₁₂-alkyl and C₆-C₁₈-alkyl which is interrupted by -O-, -CO-O- or -O-CO-, includes;
in the case where E₁ is a group of the formula Ia in which none of the radicals R₂ and R₁₄ is hydrogen, R₁ additionally has the meanings -CH₂-CH (XA) -CH₂-O-R₇, -CR₈R'₈- (CH₂) ₁- XA, -CH₂-CH (OA) -R₉ and -CH₂-CH (OH) -CH₂-XA include; and, in the case where E₁ is a group of formula Ib, R₁ additionally includes -CH₂-CH (XA) -CH₂-O-R₇;
R₂ is H, CH₃ or Cl;
R₂'-OH;
R₃ is H, -CH₃, C₁-C₄-alkoxy, C₃-alkenoxy, F, Cl, phenyl, benzyloxy or -CN;
R₃'-OH, -O-CH₂-CH (XA) -CH₂-O-R₇,

-O-CH₂- (CH₂) ₁-XA, -O-CH₂-CH (OA) -R₉, -O-CH₂-CH (OH) -CH₂-XA, or -OR₁₃₁;
R₄, R₁₄ and R₁₅ independently represent H, F, Cl, OCH₃ or CH₃;
the radicals R₄ 'and R₄''are meta to the triazine ring and, independently
each other, H, -CH₃, C₃-alkenyl, -OCH₃, C₃-alkenoxy, F, Cl, phenyl-C₃-alkyl or -CN;
R₅ is H or -CH₃;
R₆H;
R₇ is C₁-C₈alkyl, cyclohexyl, C₃-alkenyl, phenyl or benzyl;
R₈ and R₈'H;
R₉ is C₁-C₁₀ alkyl;
R₁₂ is C₁-C₁₈ alkyl, phenyl or cyclohexyl;
R _{131 is} C₃-C₁₈-alkyl or C₃-C₁₈-alkyl which is substituted by OH, C₁-C₁₈-alkoxy,
-NHCOR₁₂ and / or -OCOR₁₂; and
l is a number 1-19.

Furthermore, the invention also relates to polymeric compounds obtainable by Addition polymerization of at least one compound of formula (Id) or at least a compound of formula (Id) and at least one further ethylenically unsaturated connection

wherein the radicals
E₁ and E₂, independently of one another, each represent a group of the formula If or Ig

and wherein A is -C (= O) -CR₅ = CH-R₆;
R₁ independently of one another, -CH₂-CH (XA) -CH₂-O-R₇, -CR₈R₈ '- (CH₂) ₁-XA,
-CH₂-CH (OA) -R₉,

-CH₂-C (= CH₂) -R₁₀, - (CH₂) _p -SiR₁₁R₁₁'-CH = CH₂, C (= O) - (CH₂) _q -CH = CH₂, -CHR₈- (CH₂) _r -C (= O) -O-CH₂-CH (OH) -CH₂-OA, -CR₈R'₈- (CH₂) ₁-C (= O) -XA or -C (= O) -O-CH₂-C (= CH₂) -R₁₀; and in the event that E₁ is a group of formula If wherein none of R₂ and R₁₄ is hydrogen, R₁ additionally comprises the meanings -A and -CH₂-CH (OH) -CH₂-XA;
R₂, independently of one another, is H, C₁-C₁₂-alkyl, C₅-C₁₂-cycloalkyl, C₃-C₆-alkenyl, halogen, phenyl or trifluoromethyl; R₂ ', independently of one another, C₁-C₁₈-alkoxy, C₂-C₁₈-alkenoxy, -OH or -O-COR₁₂; R₃ and R₃ ', independently of one another, H, -OH, -OR₁, -OR₁₃₁, C₁-C₁₈-alkyl, C₃-C₁₈-alkenyl, C₆-C₁₂-cycloalkyl, halogen, trifluoromethyl, phenyl, phenyl-C₁-C₄-alkyl , -CN, C₁-C₁₈-alkyl-S (= O) _t - or phenyl-S (= O) _t -; R₄, R₄ 'and R₄'', independently of one another, H, C₁-C₁₈-alkyl, C₃-C₆-alkenyl, -OR₁₃₁, halogen, trifluoromethyl, phenyl, phenyl-C₁-C₄-alkyl, having one to three radicals C₁- C₄-alkyl-substituted phenyl-C₁-C₄-alkyl, -CN, C₁-C₁₅-alkyl-S (= O) _t - or phenyl-S (= O) _t -;
R₅ is H, -CH₂-COOR₁₃, C₁-C₄-alkyl or -CN; R₆ is H, -COOR₁₃, C₁-C₁₇-alkyl or phenyl; R₇ is C₁-C₁₈ alkyl; C₅-C₁₂ cycloalkyl; C₃-C₁₈ alkenyl; phenyl; with one to three radicals C₁-C₈-alkyl, C₁-C₈-alkoxy, C₃-C₈-alkenoxy, halogen or trifluoromethyl-substituted phenyl; Phenyl-C₁-C₄-alkyl; interrupted by one or more -O- interrupted C₃-C₅₀-alkyl; 1-adamantyl; 2-adamantyl; norbornyl; Norbornane-2-methyl; -C (= O) -R₁₂; -A;
R₈ and R₈ ', independently of one another, H, C₁-C₁₈-alkyl, phenyl, phenyl-C₁-C₄-alkyl, or with 1-3 C₁-C₈-alkyl, C₁-C₈-alkoxy, C₃-C₈-alkenoxy, halogen CF₃ substituted phenyl;
R₉ is C₁-C₁₈ alkyl, phenyl or phenyl-C₁-C₄ alkyl;
R₁₀ is H or -CH₃;
R₁₁ and R₁₁ 'are independently C₁-C₄ alkyl or phenyl or phenyl substituted with one to three C₁-C₈ alkyl, C₁-C₈ alkoxy, C₃-C₈ alkenoxy, halogen or trifluoromethyl;
R₁₂H, C₁-C₁₈ alkyl, phenyl, phenyl-C₁-C₄-alkyl, C₅-C₁₂-cycloalkyl, C₁-C₁₂-alkoxy, phenoxy, norbornan-2-yl, 5-norbornen-2-yl, 1-adamantyl ;
R₁₃ is H, C₁-C₁₈ alkyl, C₃-C₁₈ alkenyl, phenyl, C₅-C₁₂ cycloalkyl, C₃-C₅₀ alkyl interrupted by one or more -O-; with one to three radicals C₁-C₅-alkyl, C₁-C₈-alkoxy, C₃-C₈-alkenoxy, halogen or trifluoromethyl-substituted phenyl; Phenyl-C₁-C₄-alkyl, 2-adamantyl; Norbornyl, norbornane-2-methyl;
R₁₄ and R₁₅, independently of one another, H, C₁-C₁₈-alkyl, C₃-C₁₅-alkenyl, C₆-C₁₂-cycloalkyl, halogen, CF₃, phenyl, phenyl-C₁-C₄-alkyl, CN, C₁-C₁₈-alkyl-S (= O) _t - or phenyl-S (= O) _t - or -OR₁₃₁; R₁₃₁ C₁-C₁₈ alkyl; C₁-C₁₈-alkyl which is substituted by OH, C₁-C₁₈-alkoxy, C₅-C₁₂-cycloalkoxy, C₃-C₆-alkenyloxy, halogen, -COOR₁₃, -CONH₂, -COHNR₁₃₂, -CON (R₁₃₂) (R₁₃₃), -NHCOR₁₂, CN, -OCOR₁₂, phenoxy, and / or by C₁-C₁₈-alkyl, C₁-C₁₈-alkoxy or halogen-substituted phenoxy; C₃-C₁₈ alkenyl; C₆-C₁₂ cycloalkyl;
C₆-C₁₂-cycloalkyl substituted by C₁-C₄alkyl and / or -OCOR₁₂; interrupted by one or more -O- interrupted C₃-C₅₀-alkyl which is unsubstituted or substituted by OH or O-CO-R₁₂, phenyl, phenyl-C₁-C₄-alkyl, COR₁₂, SO₂R₁₂, R₁₃₂ and R₁₃₃, independently of one another, C₁ C₁₂-alkyl, C₃-C₁₂-alkoxyalkyl, C₄-C₁₆-dialkylaminoalkyl, C₅-C₁₂-cycloalkyl, or
R₁₃₂ and R₁₃₃ together C₃-C₉-alkylene, C₃-C₉-oxaalkylene or -Azaalkylen,
X is -NR₈-, -O-, -NH- (C _n H _2n ) -NH or O- (C _k H _2k ) -NH-;
k is a number 2 4,
l is a number 0-19;
m is a number 2-8;
n is a number 0-4;
p is a number 0-10;
q is a number 1-8;
pure number 0-18; and
t is a number 0, 1 or 2.

Corresponding polymers are also described below as stabilizers of the formula (Id) designated.

Examples of the radicals mentioned above in the case of the compounds of the formula (I) specified.

Among the polymeric stabilizers of formula Id are those compounds an object of separate interest obtained by polymerization of such monomeric compounds of the formula Id are obtainable, wherein R₁

-CH₂-C (= CH₂) -R₁₀, - (CH₂) _p -SiR₁₁R₁₁'-CH = CH₂, -C (= O) - (CH₂) _q -CH = CH₂, -CHR₈- (CH₂) _r -C ( = O) -O-CH₂-CH (OH) -CH₂-OA, -CR₈R'₈- (CH₂) ₁-C (= O) -XA or -C (= O) -O-CH₂-C (= CH₂ ) -R₁₀, and in the case that E₁ or E₁ and E₂ correspond to the formula Ig (of bis (2-hydroxyphenyl) triazine or tris (2-hydroxyphenyl) triazine derived compounds), R₁ additionally -CH₂-CH (XA) -CH₂ -O-R₇, -CR₈R'₈- (CH₂) ₁-XA, -CH₂-CH (OA) -R₉ and -CH₂-CH (OH) -CH₂-XA; and
in the case that E₁ is a group of formula If wherein none of R₂ and R₁₄ is hydrogen, R₁ is additionally -CH₂-CH (XA) -CH₂-O-R₇, -CR₈R'₈- (CH₂) ₁-XA, -CH₂-CH (OA) -R₉, -CH₂-CH (OH) -CH₂-XA and -A; especially those in which R₁

- (CH₂) _p -SiR₁₁R₁₁'-CH = CH₂, CHR₈- (CH₂) _r -C (= O) -O-CH₂-CH (OH) -CH₂-OA, -CR₈R'₈- (CH₂) ₁-C (= O) -XA or -C (= O) -O-CH₂-C (= CH₂) -R₁₀, and in the case that E₁ or E₁ and E₂ correspond to the formula Ig, R₁ additionally -CH₂-C (= CH₂) -R₁₀, -C (= O) - (CH₂) _q -CH = CH₂, -CH₂-CH (XA) -CH₂-O-R₇, -CR₈R'₈- (CH₂) ₁-XA, -CH₂- CH (OA) -R₉ and -CH₂-CH (OH) -CH₂-XA; and in the case that E₁ is a group of formula If wherein none of R₂ and R₁₄ is hydrogen, R₁ is additionally -CH₂-CH (XA) -CH₂-O-R₇, -CR₈R'₈- (CH₂) ₁-XA , -CH₂-CH (OA) -R₉, -CH₂-CH (OH) -CH₂-XA and -A.

Of these, especially those compounds are preferred, wherein E₁ is a group the formula If and E₂ represent a group of the formula Ig (from Bis (2-hydroxyphenyl) triazine derived compounds).

For example, polymeric compounds of the present invention are available Addition polymerization of at least one compound of formula (Ih) or at least a compound of formula (Ih) and at least one further ethylenically unsaturated connection

wherein the radicals A -C (= O) -CR₅ = CH-R₆;
R₁ independently of one another, -CH₂-CH (OA) -CH₂-O-R₇, -CHR₈- (CH₂) ₁-OA,
-CH₂-CH (OA) -R₉, -CH₂-CH (OH) -CH₂-OA,

-CH₂-C (= CH₂) -R₁₀, (CH₂) _p -SiR₁₁R₁₁'-CH = CH₂,
C (= O) - (CH₂) _p -CH = CH₂, -CHR₈- (CH₂) _p -C (= O) -O-CH₂-CH (OH) -CH₂-OA or -C (= O) -O -CH₂-C (= CH₂) -R₁₀;
R₂ and R₂ ', independently of one another, H, -OH, -OA, C₁-C₁₂-alkyl, cyclohexyl,
C₃-C₆ alkenyl, C₁-C₁₈ alkoxy, C₂-C₁₈ alkenoxy, halogen, phenyl or trifluoromethyl;
R₃ and R₃ ', independently of one another, H, -OH, -OA, -OR₁, C₁-C₁₂-alkyl, cyclohexyl,
C₃-C₆-alkenyl, C₁-C₁₈-alkoxy, C₃-C₁₈-alkenoxy, halogen, trifluoromethyl, phenyl, phenyloxy, phenyl-C₁-C₄-alkyl, phenyl-C₁-C₄-alkoxy, -CN, C₁-C₁₈-alkyl -S (= O) _t - or
Phenyl-S (= O) _t -;
R₄, R₄ 'and R₄'', independently of one another, H, C₁-C₁₂-alkyl, C₃-C₆-alkenyl, C₁-C₁₈-alkoxy, C₃-C₁₈-alkenoxy, halogen, trifluoromethyl, phenyl, phenyloxy, phenyl-C₁- C₄-alkyl, phenyl-C₁-C₄-alkyl substituted with one to three radicals C₁-C₄-alkyl, phenyl-C₁-C₄-alkoxy, -CN, C₁-C₁₈-alkyl-S (= O) _t - or phenyl- S (= O) _t -;
R₅ is H, -CH₂-COOR₁₃, C₁-C₄-alkyl or -CN;
R₆ is H, -COOR₁₃, C₁-C₁₇-alkyl or phenyl;
R₇ is C₁-C₁₈ alkyl, cyclohexyl, C₃-C₁₈ alkenyl, phenyl, having one to three radicals
C₁-C₈-alkyl, C₁-C₈-alkoxy, C₃-C₈-alkenoxy, halogen or trifluoromethyl substituted
Phenyl, phenyl-C₁-C₄-alkyl, or -C (= O) -R₁₂;
R₈ is H or C₁-C₁₈ alkyl;
R₉ is C₁-C₁₈ alkyl, phenyl or phenyl-C₁-C₄ alkyl;
R₁₀ is H or -CH₃;
R₁₁ and R₁₁ 'are independently C₁-C₄ alkyl or phenyl or phenyl substituted with one to three C₁-C₈ alkyl, C₁-C₈ alkoxy, C₃-C₈ alkenoxy, halogen or trifluoromethyl;
R₁₂ is C₁-C₁₈ alkyl, C₂-C₁₈ alkenyl or phenyl;
R₁₃ is H, C₁-C₁₈ alkyl, C₃-C₁₈ alkenyl or phenyl;
l is a number 0-19;
p is a number 0-10;
q is a number 1-8;
r is a number 0-18; and
t is a number 0, 1 or 2.

Preferred meanings of the radicals in formula Id are listed below:

Preferably, R₁ is -CH₂-CH (XA) -CH₂-O-R₇, -CR₈R'₈- (CH₂) ₁-XA,
-CH₂-CH (OA) -R₉,

-CHR₈- (CH₂) _r -C (= O) -O-CH₂-CH (OH) -CH₂-OA; particularly preferably -CH₂-CH (OA) -CH₂-O-R₇, -CHR₈- (CH₂) ₁-OA, -CH₂-CH (OA) -R₉,

or -CHR₈- (CH₂) _r -C (= O) -O-CH₂-CH (OH) -CH₂-OA; and most preferably -CH₂-CH (OA) -CH₂-O-R₇, -CHR₈- (CH₂) ₁-OA, -CH₂-CH (OA) -R₉ or

Preferably, R₂ is H, C₁-C₄ alkyl, C₃ alkenyl, F, Cl or phenyl; especially preferably H, -CH₃ or Cl; and most preferably H or -CH₃.

Preferably, R₂ 'is -OH, C₁-C₄-alkoxy, C₃-alkenoxy; especially C₁-C₂-alkoxy, or -OH.

R₃ or R₃ is preferably H, -OH, -OR₁, -OR₁₃₁, C₁-C₄-alkyl, cyclohexyl, C₃ alkenyl, F, Cl, trifluoromethyl, phenyl, benzyl or -CN; particularly preferably H, -OH, -OR₁, -CH₃, C₁-C₁₂-alkoxy, substituted by C₂-C₆-alkanoyloxy C₂-C₁₈ alkoxy, C₃-alkenoxy, F, Cl, phenyl, benzyloxy or -CN; and especially preferably H, -OH, -OR₁, -CH₃, C₁-C₁₂-alkoxy, Cl, phenyl or -CN.

Frequently R₃ 'is -OH, -OR₁ or -OR₁₃₁, and R₃ does not mean -OR₁.

Preferably, R₄, R₄ 'or R₄' 'is H, C₁-C₄alkyl, C₃-alkenyl, C₁-C₄alkoxy, C₃-alkenoxy, F, Cl, trifluoromethyl, phenyl, phenyl-C₁-C₃-alkyl or -CN; especially preferably H, -CH₃, C₃-alkenyl, -OCH₃, C₃-alkenoxy, F, Cl, phenyl-C₃-alkyl or -CN; and most preferably H or -CH₃.  

Preferably, R₅ is H or -CH₃.

Preferably, R₆ is H, -COOR₁₃, -CH₃ or phenyl; and particularly preferably H or -CH₃.

Preferably, R₇ is C₁-C₈ alkyl, cyclohexyl, C₃-C₈ alkenyl, phenyl, with one to three Rests C₁-C₄-alkyl or C₁-C₄-alkoxy-substituted phenyl or benzyl; and especially preferably C₁-C₈-alkyl, cyclohexyl, C₃-alkenyl, phenyl or benzyl.

Preferably R₈ and R₈ ', independently of one another, are H or C₁-C₈-alkyl.

R₁₀ is preferably hydrogen.

R₁₁ and R₁₁ 'are, independently of each other, preferably C₁-C₄ alkyl or phenyl, before all methyl.

X is preferably -O- or -NR₈-, especially an oxygen atom.

The value of the index 1 is preferably 1-15.

Preference is given to compounds of the formula (Id) in which the radicals
R₁ independently of one another, -CH₂-CH (XA) -CH₂-O-R₇, -CR₈R₈ '- (CH₂) ₁-XA,

or
-CHR₈- (CH₂) _r -C (= O) -O-CH₂-CH (OH) -CH₂-OA;
R₂ is H, C₁-C₄ alkyl, C₃ alkenyl, F, Cl or phenyl;
R₂ 'C₁-C₄ alkoxy, C₃ alkenoxy, -OA, -O-COR₁₂ or -OH;
R₃ and R₃ 'are independently H, -OH, -OR₁, -OR₁₃₁, C₁-C₄alkyl, cyclohexyl, C₃-alkenyl, F, Cl, trifluoromethyl, phenyl, benzyl or -CN;
R₄ 'and R₄'', independently of one another, H, C₁-C₄-alkyl, C₃-alkenyl, C₁-C₄-alkoxy, C₃-alkenoxy, F, Cl, trifluoromethyl, phenyl, phenyl-C₁-C₃-alkyl or -CN ;
R₅ is H or -CH₃;
R₆ is H, -COOR₁₃, -CH₃ or phenyl;
R₇ is C₁-C₅-alkyl, cyclohexyl, C₃-C₈-alkenyl, phenyl, substituted with one to three radicals C₁-C₄-alkyl or C₁-C₄-alkoxy-substituted phenyl; or benzyl;
R₈ and R₈ ', independently of one another, are H or C₁-C₁₈-alkyl;
R₉ is C₁-C₁₀ alkyl, phenyl or benzyl;
R₁₂H, C₁-C₁₈-alkyl, phenyl, phenyl-C₁-C₄-alkyl or cyclohexyl;
R₁₃ is C₁-C₄alkyl, C₃-alkenyl, cyclohexyl, phenyl-C₁-C₄alkyl or phenyl;
R₄, R₁₄ and R₁₅, independently, H, F, Cl, C₁-C₄ alkoxy, CF₃, phenyl, CN or C₁-C₈ alkyl;
R₁₃₁ C₁-C₁₈ alkyl; C₃-C₁₈alkyl which is substituted by OH, C₁-C₁₈alkoxy, C₅-C₁₂-cycloalkoxy, -COOR₁₃, -CONH₂, -COHNR₁₃₂, -CON (R₁₃₂) (R₁₃₃), -NHCOR₁₂, CN, -OCOR₁₂ and / or phenoxy; C₃ alkenyl; C₆-C₁₂ cycloalkyl; interrupted by one or more -O- interrupted C₃-C₅₀-alkyl which is unsubstituted or substituted by OH or O-COR₁₂; phenyl; Phenyl-C₁-C₄-alkyl; -COR₁₂; -SO₂R₁₂;
X is -O- or -NR₈-;
l is a number 1-19; and
r is a number 0-10.

Particular preference is given to polymers comprising units of the formula Id, in which the radicals A are -C (= O) -CR₅ = CH-R₆;
R₁ independently of one another, -CH₂-CH (OA) -CH₂-O-R₇, -CH₂-CH (OA) -R₉,

or -CHR₈- (CH₂) ₁-OA;
R₂ is H, CH₃, OCH₃, C₃-alkenoxy or Cl;
R₂'-OH;
R₃ is H, -CH₃, C₁-C₄-alkoxy, C₃-alkenoxy, F, Cl, phenyl, benzyloxy or -CN;
R₃'-OR₁ or -OR₁₃₁;
R₄, R₁₄ and R₁₅, independently, H, F, CL, phenyl, CN, OCH₃ or CH₃;
R₄ 'and R₄'', independently of one another, H, -CH₃, C₃-alkenyl, -OCH₃, C₃-alkenoxy, F, Cl,
Phenyl-C₃-alkyl or -CN;
R₅ is H or -CH₃;
R₆ is H or -CH₃;
R₇ is C₁-C₈alkyl, cyclopentyl, cyclohexyl, C₃-alkenyl, phenyl or benzyl;
R₈ is H or C₁-C₁₈ alkyl;
R₉ is C₁-C₁₀ alkyl or phenyl;
R₁₂ is C₁-C₁₈ alkyl, phenyl or cyclohexyl;
R₁₃₁ C₃-C₁₈ alkyl or C₃-C₁₈ alkyl which is substituted by C₁-C₁₈ alkoxy, OH, phenoxy, -NHCOR₁₂ and / or -OCOR₁₂; and
l is a number 1-19;
especially those in which the radicals A -C (= O) -CR₅ = CH-R₆;
R₁ independently of one another, -CH₂-CH (OA) -CH₂-O-R₇, -CH₂-CH (OA) -R₉,

or -CH₂- (CH₂) ₁-OA;
R₂ is H or CH₃;
R₂'-OH;
R₃ is H, -CH₃, Cl or phenyl;
R₃'-OR₁ or -OR₁₃₁;
R₄ is H or CH₃;
R₄ ', R₄'', R₁₄ and R₁₅ hydrogen;
R₅ is H or -CH₃;
R₆ H;
R₇ is C₁-C₈ alkyl;
R₉ is C₁-C₁₀ alkyl;
R₁₂ C₁-C₈ alkyl;
R _{131 is} C₃-C₁₈alkyl or C₃-C₁₈alkyl which is substituted by -OCOR₁₂; and
l is a number 1-10.

Especially preferred are polymers containing units of the formula (Id) in which at least one of the radicals R₃ or R₃ 'has the meaning -OR₁.

An object of particular interest is forming polymers according to the invention Units of the formula Id, wherein E₁ of the formula If and E₂ corresponds to the formula Ig. among them especially mixed substituted compounds are preferred in which neither R₃ nor R₃ 'the Meaning -OR₁; especially those in which R₂ 'represents OH and R₃' C₁-C₁₈ alkoxy, or C₂-C₁₈ alkoxy, which is interrupted by -O- or by -OCOR₁₂ and / or C₁-C₁₈-alkoxy or C₅-C₁₂-cycloalkoxy is substituted, wherein R₁₂ C₁-C₁₈ alkyl, phenyl, phenyl-C₁-C₄-alkyl or C₅-C₁₂-cycloalkyl; These are above all those compounds in which R₁ has the meaning -CR₈R₈ '- (CH₂) ₁-XA.  

There are both homopolymers and copolymers in question, the Copolymers of at least two different compounds (structural units) of Formula (Id) may be constructed or from at least one compound of the formula (Id) and another comonomer (ethylenically unsaturated compound). Also the Compounds of the formula I can be used for the preparation of the inventive Homopolymers as well as copolymers are used.

Of special technical interest, polymeric compounds are also available by copolymerization of at least two different compounds of formula (Id).

As further comonomers (comonomers different from compounds of the formula (Id)) are, inter alia: acrylic acid, methacrylic acid, acrylates, methacrylates, Acrylamides, methacrylamides, vinyl ethers, styrene, styrene derivatives, vinylpyridines, Acrylonitrile, methacrylonitrile, vinylpyrrolidone, derivatives of vinylpyrrolidone, as well ethylenically unsaturated derivatives of sterically hindered amines, 2- (2'-hydroxyphenyl) benzotriazoles, 2-hydroxybenzophenones or sterically hindered Phenols.

Of particular importance is the use of other copolymerizable stabilizers, in For example, of ethylenically unsaturated derivatives of sterically hindered amines (HALS), 2- (2'-hydroxyphenyl) benzotriazoles, 2-hydroxy-benzophenones or steric hindered phenols. | 10 |

In copolymers, which in addition to units of at least one compound of formula Id contain further comonomers and which are used as light stabilizers, is the ratio of other comonomers: monomers of the formula Id preferably up to 10: 1; It is mainly in the range 1: 1 to 5: 1.

Corresponding, useful as comonomer HALS are generally by the structural element

characterized in that the three open bonds are saturated by H or an organic chemical substituent and at least one polymerizable, ethylenically unsaturated double bond is contained in the molecule;
Such compounds are described, inter alia, in US-A-4,942,238, US-A-4,983,737 and EP-A-634,399 and literature cited therein.

Corresponding comonomer usable 2- (2'-hydroxyphenyl) benzotriazoles generally by the structural element

characterized, wherein the four open bonds through H or an organic-chemical substituent are saturated and at least one polymerizable, ethylenically unsaturated Double bond is contained in the molecule; corresponding compounds are under et al. in US-A-5099027, US-A-4528311, US-A-5147902, Research Disclosure 32592, US-A-4785063, US-A-4892915, US-A-4611061, EP-A-190003, EP-A-508744, US-A-4716234, US-A-3493539, US-A-5234807, US-A-5256359, US-A-5385815, US-A-5372922, JP-A-03-139590, EP-A-431868, JP-A-03-8547, GB-A-2232667, EP-A-282294, EP-A-343996, EP-A-133164, EP-A-131468, J. Macromol. Sci., Pure Appl. Chem. A30 (9-10), 741 (1993) and Polm. Bull. 12 (5), 375 (1984), as well as cited therein Literature described.

Corresponding comonomer usable 2-hydroxybenzophenones are general through the structural element

characterized, wherein the four open Bonds are saturated by H or an organic-chemical substituent and at least one polymerizable, ethylenically unsaturated double bond in the molecule is included; Such compounds are disclosed, inter alia, in CH-B-383001 and US Pat CH-B-376899 and literature cited therein.

Corresponding steric hindered phenols useful as comonomers are general through the structural element

characterized in that the three open Bindings are saturated by organic chemical substituents and at least one polymerizable, ethylenically unsaturated double bond is contained in the molecule, usually in the hydroxyl group p-substituent; corresponding compounds are in, inter alia, US-A-3,708,520 and literature cited therein.

Preference is given as further comonomers (compounds of the formula (Id) different comonomers) and compounds of the following formulas (II) - (VII)
(II) R₁₈-CH = C (R₁₇) -C (= O) -X'-R₂₀,
wherein X 'is -O- or -NR₁₉-;
R₁₇H, C₁-C₄ alkyl, -CH₂-COOR₂₁, -Cl or -CN;
R₁₈H, -COOR₂₁ or -CH₃;
R₁₉H, C₁-C₈-alkyl, C₄-C₁₂-cycloalkyl, by -N (R _X ) ₂ substituted C₁-C₄-alkyl, -S (= O) -R _X , -C (CH₃) ₂-CH₂C (= O ) -CH₃,
-C (CH₃) ₂-CH₂-SO₃M, - (CH₂) _s -SO₃M or

R₂₀H; C₁-C₁₈ alkyl; C₂ to C₁₈ alkenyl; interrupted by one or more O atoms C₂-C₁₈-alkyl which may be substituted by OH; or
- (CH₂) _s -SO₃M;

-CH₂F; -CH₂Cl; -CH₂CN; -CH₂CH₂Cl;
-CH₂CH₂CN; -CH₂CH₂-COOR _X ; C₇-C₁₁ phenylalkyl; naphthyl; by -N (R _X ) ₂ substituted C₁-C₄-alkyl; adamantyl; C₆-C₁₂ cycloalkyl;
R₂₁H, C₁-C₁₈ alkyl, phenyl or C₂-C₁₈ alkenyl;
R _{X is} C₁-C₄ alkyl or phenyl;
R _{Y is} H, C₁-C₁₂-alkyl, phenyl, -CO-OR _X , -CN, -F, -Cl;
MH or an alkali metal; and
s mean a number between 1 and 5.
(III) R₂₂-C (= O) -O-CH = CH₂,
wherein R₂₂ is C₁-C₁₉-alkyl or phenyl.
(IIIa) _R22a -O-CH = CH₂,
wherein R _{22a is} C₁-C₁₈ alkyl.

wherein R₂₃ is H or -CH₃;
R₂₄ is H, -CR₂₃ = CH₂, -C (O) -phenyl or -SO₃M; and
MH or an alkali metal means.

wherein R₂₅ is H or -CH₃.
(VI) CH₂ = CR₂₆-R₂₇,
wherein R₂₆ is H, -F, -Cl or -CH₃ and R₂₇-Cl, -Br, -F or CN.

and the above-mentioned polymerizable ethylenically unsaturated derivatives of sterically hindered amines (HALS), 2- (2'-hydroxyphenyl) benzotriazoles, 2-hydroxy benzophenones and hindered phenols.

Preferred comonomers of the formulas (II) - (VII) are:
(II) R₁₈-CH = C (R₁₇) -C (= O) -X-R₂₀,
wherein R₁₇ is H, -CH₃, -CH₂-COOR₂₁ or -CN;
R₁₈ H, -COOR₂₁ or -CH₃;
R₁₉ is H, C₁-C₄alkyl, -C (CH₃) ₂-CH₂-C (= O) -CH₃, -C (CH₃) ₂-CH₂-SO₃M or - (CH₂) _s -SO₃M;
R₂₀ H, C₁-C₁₈-alkyl, interrupted by one or more O atoms C₂-C₃₀-alkyl or - (CH₂) _s -SO₃M;
R₂₁ is H, C₁-C₁₈ alkyl, phenyl or C₂-C₁₈ alkenyl;
MH or an alkali metal
X is -O- or -NR₁₉-; and
s mean a number between 1 and 5.
(III) R₂₂-C (= O) -O-CH = CH₂,
wherein R₂₂ is C₁-C₁₉-alkyl or phenyl.
(IIIa) _R22a -O-CH = CH₂,
wherein R _{22a is} C₁-C₈-alkyl.

wherein R₂₃ is H or -CH₃;
R₂₄ is H, -CR₂₃ = CH₂, -C (O) -phenyl or -SO₃M; and
MH or an alkali metal means.

wherein R₂₅ is H or -CH₃.
(VI) CH₂ = CR₂₆-CN,
wherein R₂₆ is H or -CH₃.

The possible meanings for the substituents in the formulas (II) - (VII) correspond those as indicated above for the compounds of the formula (I) or (Id).

If substituents in the above formulas are alkyl which is interrupted by one or more O atoms and has up to 18 carbon atoms, then radicals such as - (CH₂-CH₂-O) _1-8 -CH₃, - (CH₂-CH₂-O) _{1-8 are used} -C₂H₅ or - (CH₂-CH₂-CH₂-O) _1-5 -CH₃ in question.

Substituents in the above formulas mean alkali metals, so comes Li, Na or K. in question.

Particularly preferred further comonomers (comonomers other than compounds of the formula (Id)) are compounds of the formulas (II) - (IV) and (VII)
Preference is given to copolymers obtainable by polymerization of at least one preferred compound of the formula (Id) and at least one of the comonomers of the formulas (II) - (VII).

Particular preference is given to copolymers which are obtained by polymerization of at least one particularly preferred compound of formula (Id) and at least one of Comonomers of formulas (II) - (IV) or (VII) are available.

Very particular preference is given to copolymers which are prepared by polymerization of at least one very particularly preferred compound of the formula (Id) and at least one of the comonomers of the formulas (II) - (IV) or (VII)
in which
R₁₇ is H or -CH₃;
R₁₈ is H or -CH₃;
R₁₉ is H, C₁-C₄ alkyl, -C (CH₃) ₂-CH₂-SO₃M or - (CH₂) _s -SO₃M;
R₂₀ H, C₁-C₈-alkyl or interrupted by one or more O atoms C₂-C₂₀-alkyl;
R₂₂ -CH₃;
R _{22a is} C₁-C₄ alkyl;
R₂₃ and R₂₄ H;
MH, Li, Na or K.
X is -O- or -NR₁₉-; and
s is the number 2 or 3;

are available.

The compounds of formula (I) or (Id) can be in principle produce known methods. The following reaction schemes show in principle, two-stage (a + b) process for the preparation of compounds of the formula (I) or (Id), which are derived from Monoresorcinoltriazinen. Analog can be synonymous produce compounds derived from bis- or trisresorcinol. Further explanations for possible manufacturing processes, see EP-A-0 434 608.

• a) Alkylation of the para-OH group of the resorcinol residue (by, for example, a glycidyl ether or a ω-bromoalcohol): (Ar: substituted or unsubstituted phenyl radical; R: for example alkyl radical) (Ar: substituted or unsubstituted phenyl radical; i: 1-20)
• b) Acrylating or methacrylating the aliphatic OH group (Ar: substituted or unsubstituted phenyl radical; R: for example, alkyl; R₁: H or -CH₃) (Ar: substituted or unsubstituted phenyl radical; i: 1-20; R₁: H or -CH₃)

Serving as starting compounds Resorcinoltriazine of the formula  

can also be prepared by known methods or by analogy with (EP-A-434 608, H. Brunetti and C.E. Lüthi, Helv. Chim. Acta 55, 1566 (1972); EP-A-577 559; GB-A-884 802).

The polymerization (addition polymerization) of one of the monomeric compounds of Formula (Id) can be initiated by free radical, anionic or cationic initiators become. Radical initiators which are used in heating in Radicals decay, such as. As organic peroxides or hydroperoxides, azo compounds or redox catalysts. The polymerization can also be caused by high-energy radiation be initiated. The polymerization may be in solution, emulsion, dispersion or in bulk be executed. The skilled worker is aware of these methods. Continue to be in EP-A-0 577 122 page 9, line 46 to page 10, line 35 Polymerization described.

Examples of compounds of the formula (I) are:

Examples of monomers of the formula (Id) are, in addition to the above, the following Links:

Examples of polymers of compounds of the formula (Id) are:
(600) Homopolymer of Compound (204)
(601) Copolymer of compound (204) and n-butyl acrylate in the molar ratio 1: 4
(602) Homopolymer of Compound (207)
(603) Copolymer of compound (207) and n-butyl acrylate in the molar ratio 1: 4
(604) Homopolymer of Compound (504)
(605) Copolymer of compound (504) and n-butyl acrylate in molar ratio 1: 4 (606) copolymer of compound (504) and n-dodecyl methacrylate in molar ratio 1: 4
(607) Homopolymer of Compound (102)
(608) Copolymer of compound (102) and n-butyl acrylate in the molar ratio 1: 4
(609) Homopolymer of Compound (402)
(610) Copolymer of compound (402) and n-butyl acrylate in molar ratio 1: 2
(611) Homopolymer of Compound (103)
(612) Copolymer of compound (103) and n-butyl acrylate in molar ratio 1: 2
(613) Homopolymer of Compound (400)
(614) Copolymer of compound (400) and n-butyl acrylate in molar ratio 1: 2
(615) Copolymer of compound (105) and n-butyl acrylate in molar ratio 1: 2
(616) Copolymer of compound (405) and n-butyl acrylate in molar ratio 1: 2.

In addition to the copolymers of the invention mentioned above, compounds of the formula (I) can also be incorporated by copolymerization into those polymers which are prepared by polymerization of ethylenically unsaturated monomers. These include, for example, the following monomers:
Acrylic acid, methacrylic acid, esters of acrylic and methacrylic acid, amides of acrylic and methacrylic acid, acrylonitrile, styrene, α-methylstyrene, butadiene, isoprene, maleic anhydride, esters, amides and imides of maleic acid, vinyl chloride, vinylidene chloride, vinyl acetate, vinyl butyral, vinyl alkyl ethers or N-vinylpyrrolidone. Preference is given to the incorporation in such polymers, which are composed of acrylic acid, methacrylic acid, esters or amides of acrylic or methacrylic acid, styrene or acrylonitrile. The polymer may be composed of one or more such monomers. The addition of the unsaturated compound of the formula (I) takes place during the polymerization, so that a copolymerization takes place.

The polymerization can be carried out by free-radical, anionic or cationic initiators be initiated. Radical initiators are preferably used when heated decompose into radicals, such as. As organic peroxides or hydroperoxides, azover bonds or redox catalysts. The polymerization can also be carried by high-energy Radiation are initiated, such. B. also in radiation-curable paints (UV-curable or ESR-curable). In this case, the copolymerizable hydroxyphenyl-s-triazine during the Film formation built into the paint matrix.

Particularly suitable for such copolymerizations is the process of group transfer polymerization. Here, by using certain initiators a "living" Polymer formed. Examples of suitable initiators are 1-trimethylsiloxy-1 alkoxy-2-methylpropene. The process of group transfer polymerization has been around A few years ago, for example, in US-A-4,695,607 and US-A-4,414,372 wrote.

The polymerization can be carried out in solution, emulsion, dispersion or in bulk become. The skilled worker is aware of these methods.

For incorporation by copolycondensation or copolyaddition are especially those Compounds of formula (I) which contain two functional groups. Should only small amounts of a compound of formula (I) by polycondensation or Polyaddition be incorporated, so are also those compounds of formula (I) in Question that contain only one functional group.

Mono-, di- or trisfunctional compounds of the formula (I) can, for. In polyester, Polyether esters, polyamides, polyurethanes, polycarbonates, epoxy resins, phenolic resins, Melamine resins or alkyd resins are incorporated. The installation is made by adding the preparation of the condensation or addition polymers according to the this Specialist methods known.

The incorporation can also take place in oligomeric or polymeric intermediates. For example  can unsaturated compounds of formula (I) to unsaturated polyester resins and their mixtures with other vinyl compounds are added and then under Zu Curing radical initiators are cured. Or oligomeric epoxy resins can with functional compounds of the formula (I) are reacted and then with cured an epoxy hardener. Or OH-functional compounds of the For mel (I) can be reacted with melanin resins and the resulting verb then cured with the addition of acrylic resins.

Also, the incorporation into polyurethanes, phenolic resins or alkyd resins can with a precursor (precursor) happen before the final curing of the resin. The curing of the Resin can also be carried out under acidic or basic catalysis without the Interfere with triazine compounds.

Another possibility of installation is the reaction of a compound of Formula (I) with a polymer containing suitable functional groups. This can z. As polymers with hydroxyl, carboxyl, anhydride, amino, epoxy or iso be cyanate groups. Examples of these are copolymers of acrylic and methacrylic acid, of hydroxyalkyl (meth) acrylates, of glycidyl (meth) acrylates, partially hydrolyzed polyvinyl acetate or ethylene-vinyl acetate copolymer, partially esterified Cellulose, partially hydrolyzed polyalkyl (meth) acrylates, polyesters or polyurethanes with reactive end groups, epoxy resins or copolymers of maleic acid, of maleic acid anhydrides or maleic monoesters or half-amides.

For the implementation of such compounds of formula (I) are in question, which is a functional group containing the functional groups of the polymer can react. This can z. As hydroxyl, carboxyl, ester, amino, epoxy or Be isocyanate groups. If you z. B. a polymer containing OH groups, with a To modify compound of formula (I), so you can, for example, a compound of formula (I) containing at least one isocyanate, epoxide, carboxyl or Contains ester group. A polymer containing epoxide groups may, for. B. with a Compound of formula (I) are reacted, the at least one hydroxyl, carboxyl or Contains amino group. A copolymer of maleic anhydride may, for. B. with a Compound of formula (I) are reacted, which is a hydroxyl, amino or Contains epoxide group.

These reactions are followed by the commonly used methods for polymer homologues  Implementations carried out. Preferably, the reaction is carried out in solution. you can all functional groups of the polymer or only part of it realize. Thereafter, the amount of the compound used for the implementation of the Formula (I). In the examples below, details for such conversions are given described.

A special method for incorporation into polymers is the grafting of ethylenic unsaturated derivatives of the formula (I) on hydrocarbon polymers. The verbin Formulations of the formula (I) which contain ethylenically unsaturated groups were previously already defined in more detail. Hydrocarbon polymers can be saturated or unsaturated his. The former include the polyolefins, such as. As polyethylene, polypropylene, polybutene or polyisobutene. The latter include the diene polymers and their copolymers with olefins, such as. As polybutadiene, polyisoprene, propylene-butadiene or ethylene Propylene-butadiene. Preferably, the grafting on polyolefins, in particular on Polyethylene.

The grafting reaction can be carried out in solution or in bulk. As catalysts one uses radical formers, as well as for the homo- or copolymerization unsaturated compound can be used.

All of these methods for incorporation of compounds of formula (I) into polymers can be carried out with a relatively small amount of the triazine, for example with 0.05 to 5 wt .-%, based on the modified polymer. These quantities give the Polymer resistance to damage from light, oxygen and heat, wherein this stabilization is not lost by emigration or elution of the stabilizer can. Preference is given for this purpose, 0.1 to 3 wt .-% of a compound of Incorporated formula (I).

But you can also incorporate larger amounts of triazine by these methods, for example 5 to 50 wt .-%, based on the modified polymer. This is then makes sense, if the so modified polymers as polymeric stabilizers wants to use. These polymeric stabilizers can be organic materials, in particular organic polymers. The polymeric stabilizers but can also be applied as a thin protective layer on plastic moldings, for example, in dissolved form or by coextrusion, as z. In US-A-4,676,870 is described.  

Another application of these methods is the incorporation of compounds of the formula (I) in polymer microparticles. EP-A-226 538 discloses the incorporation of sunscreen agents Copolymerization or copolycondensation in such microparticles described as disperse phase can be used in coatings. In this case you build in the Microparticles 0.1 to 30 wt .-% of a compound of formula (I), preferably 0.5 to 10 wt .-%, based on the modified polymer.

For the incorporation into microparticles can advantageously the method of Group transfer polymerization can be used, as z. In EP-A-293 871 is described.

The invention also relates to those produced by the described method modified polymers containing a compound of formula (I) in the Contain weights in chemically bound form and thereby against damage stabilized by light, oxygen and heat.

The stabilizers according to the invention of the formula I, the formula Id and the Invention According to modified polymers can be added with various additives, such as this is common in the technology of polymers. These additives can stabilizers or processing aids or pigments or other additives. Examples of this are the following accessories.

1. Antioxidants

• 1.1. Alkylated monophenols, e.g. For example, 2,6-di-tert-butyl-4-methylphenol, 2-butyl-4,6-di methylphenol, 2,6-di-tert-butyl-4-ethylphenol, 2,6-di-tert-butyl-4-n-butylphenol, 2,6-di- tert -butyl-4-iso-butylphenol, 2,6-di-cyclopentyl-4-methylphenol, 2- (α-methylcyclo hexyl) -4,6-dimethylphenol, 2,6-dioctadecyl-4-methylphenol, 2,4,6-tri-cyclohexylphenol, 2,6-di-tert-butyl-4-methoxymethylphenol, linear or branched in the side chain No nylphenols such. As 2,6-di-nonyl-4-methylphenol, 2,4-dimethyl-6- (1'-methyl-undec-1'- yl) -phenol, 2,4-dimethyl-6- (1'-methyl-heptadec-1'-yl) -phenol, 2,4-dimethyl-6- (1'- methyl-tridec-1'-yl) -phenol and mixtures thereof.
• 1.2. Alkylthiomethylphenols, eg. B. 2,4-dioctylthiomethyl-6-tert-butylphenol, 2,4-di-oc tylthiomethyl-6-methylphenol, 2,4-dioctylthiomethyl-6-ethylphenol, 2,6-di-dodecylthio  methyl-4-nonylphenol.
• 1.3. Hydroquinones and alkylated hydroquinones, e.g. B. 2,6-di-tert-butyl-4-methoxyphenol, 2,5-di-tert-butyl-hydroquinone, 2,5-di-tert-amyl-hydroquinone, 2,6-diphenyl-4-octadecyl oxyphenol, 2,6-di-tert-butyl-hydroquinone, 2,5-di-tert-butyl-4-hydroxyanisole, 3,5-di-tert-butyl butyl-4-hydroxyanisole, 3,5-di-tert-butyl-4-hydroxyphenyl-stearate, bis (3,5-di-tert-butyl-4-) hydroxyphenyl) adipate.
• 1.4. Tocopherols, e.g. B. α-tocopherol, β-tocopherol, γ-tocopherol, δ-tocopherol and Mi of it (vitamin E).
• 1.5. Hydroxylated thiodiphenyl ethers, e.g. B. 2,2'-thio-bis (6-tert-butyl-4-methylphenol), 2,2'-thio-bis (4-octylphenol), 4,4'-thio-bis (6-tert-butyl-3-methylphenol), 4,4'-thio-bis- (6-tert-butyl-2-methylphenol), 4,4'-thio-bis (3,6-di-sec-amylphenol), 4,4'-bis (2,6-di methyl-4-hydroxyphenyl) disulfide
• 1.6. Alkylidene Bisphenols, e.g. B. 2,2'-methylene-bis (6-tert-butyl-4-methylphenol), 2,2'- Methylene-bis (6-tert-butyl-4-ethylphenol), 2,2'-methylenebis [4-methyl-6- (α-methylcyclo hexyl) -phenol], 2,2'-methylenebis (4-methyl-6-cyclohexylphenol), 2,2'-methylene-bis (6- nonyl-4-methylphenol), 2,2'-methylenebis (4,6-di-tert-butylphenol), 2,2'-ethylidene-bis- (4,6-di-tert-butylphenol), 2,2'-ethylidene-bis (6-tert-butyl-4-isobutylphenol), 2,2 '⁸⁷¹⁵⁸ ⁰⁰⁰⁷⁰ ⁵⁵² ⁰⁰¹⁰⁰⁰²⁸⁰⁰⁰⁰⁰00200012000285918704700040 0002019536730 00004 87039-Methy len-bis [6- (α-methylbenzyl) 4-nonylphenol], 2,2'-methylenebis [6- (α, α-dimethylbenzyl) - 4-nonylphenol], 4,4'-methylenebis (2,6-di-tert-butylphenol), 4,4'-methylene-bis (6-tert-bu tyl-2-methylphenol), 1,1-bis (5-tert-butyl-4-hydroxy-2-methylphenyl) -butane, 2,6-bis (3-yl) tert -butyl-5-methyl-2-hydroxybenzyl) -4-methylphenol, 1,1,3-tris (5-tert-butyl-4-hydroxy) 2-methylphenyl) butane, 1,1-bis (5-tert-butyl-4-hydroxy-2-methylphenyl) -3-n-dodecylmer captobutane, ethylene glycol bis [3,3-bis (3'-tert-butyl-4, -hydroxyphenyl) -butyrate], bis (3-tert. tert-butyl-4-hydroxy-5-methylphenyl) dicyclopentadiene, bis [2- (3-tert-butyl-2-hydroxy) 5-methylbenzyl) -6-tert-butyl-4-methylphenyl] terephthalate, 1,1-bis (3,5-dimethyl-2- hydroxyphenyl) butane, 2,2-bis (3,5-di-tert-butyl-4-hydroxyphenyl) -propane, 2,2-bis (5-tert. butyl-4-hydroxy-2-methylphenyl) -4-n-dodecylmercapto-butane, 1,1,5,5-tetra- (5-tert-butyl) butyl-4-hydroxy-2-methylphenyl) pentane.
• 1.7. O, N and S benzyl compounds, e.g. B. 3,5,3 ', 5'-tetra-tert-butyl-4,4'-dihydroxydiben ethyl ether, octadecyl-4-hydroxy-3,5-dimethylbenzyl-mercaptoacetate, tridecyl-4-hydroxy 3,5-di-tert-butylbenzyl-mercaptoacetate, tris (3,5-di-tert-butyl-4-hydroxybenzyl) -amine,  Bis (4-tert-butyl-3-hydroxy-2,6-dimethylbenzyl) dithioterephthalate, bis (3,5-di-tert-butyl) 4-hydroxybenzyl) sulfide, isooctyl-3,5-di-tert-butyl-4-hydroxybenzyl mercaptoacetate.
• 1.8. Hydroxybenzylated malonates, e.g. For example, dioctadecyl-2,2-bis (3,5-di-tert-butyl-2-hydroxy benzyl) malonate, di-octadecyl-2- (3-tert-butyl-4-hydroxy-5-methylbenzyl) malonate, Di dodecylmercaptoethyl 2,2-bis (3,5-di-tert-butyl-4-hydroxybenzyl) -malonate, di- [4- (1,1,3,3-tetramethylbutyl) phenyl] -2,2-bis malonate (3,5-di-tert-butyl-4-hydro xybenzyl-).
• 1.9. Hydroxybenzyl aromatics, e.g. B. 1,3,5-tris (3,5-di-tert-butyl-4-hydroxybenzyl) -2,4,6- trimethylbenzene, 1,4-bis (3,5-di-tert-butyl-4-hydroxybenzyl) -2,3,5,6-tetramethylbenzene, 2,4,6-tris (3,5-di-tert-butyl-4-hydroxybenzyl) phenol.
• 1.10. Triazine compounds, e.g. For example, 2,4-bis-octylmercapto-6- (3,5-di-tert-butyl-4-hydroxy anilino) -1,3,5-triazine, 2-octylmercapto-4,6-bis (3,5-di-tert-butyl-4-hydroxyanilino) -1,3,5- triazine, 2-octylmercapto-4,6-bis (3,5-di-tert-butyl-4-hydroxyphenoxy) -1,3,5-tr-iazine, 2,4,6- Tris (3,5-di-tert-butyl-4-hydroxyphenoxy) -1,2,3-triazine, 1,3,5-tris (3,5-di-tert-butyl-4-) hydroxybenzyl) isocyanurate, 1,3,5-tris (4-tert-butyl-3-hydroxy-2,6-dimethylbenzyl) iso cyanurate, 2,4,6-tris (3,5-di-tert-butyl-4-hydroxyphenylethyl) -1,3,5-triazine, 1,3,5-tris (3,5- di-tert-butyl-4-hydroxyphenylpropionyl) -hexahydro-1,3,5-triazine, 1,3,5-tris (3,5-dicyclo hexyl-4-hydroxybenzyl) isocyanurate.
• 11.1. Benzylphosphonates, e.g. Dimethyl 2,5-di-tert-butyl-4-hydroxybenzylphosphonate, Diethyl 3,5-di-tert-butyl-4-hydroxybenzylphosphonate, dioctadecyl-3,5-di-tert-butyl-4- hydroxybenzylphosphonate, dioctadecyl-5-tert-butyl-4-hydroxy-3-methylbenzylphos phonate, Ca salt of 3,5-di-tert-butyl-4-hydroxybenzylphosphonic acid monoethyl ester.
• 1.12. Acylaminophenols, e.g. 4-hydroxy-lauric acid anilide, 4-hydroxystearic acid anilide, N- (3,5-di-tert-butyl-4-hydroxyphenyl) -carbaminsäureoctylester.
• 1.13. Esters of (3- (3,5-di-tert-butyl-4-hydroxyphenyl) propionic acid with one or more valent alcohols, such as. With methanol, ethanol, n-octanol, i-octanol, octadecanol, 1,6-hexanediol, 1,9-nonanediol, ethylene glycol, 1,2-propanediol, neopentyl glycol, thiodi ethylene glycol, diethylene glycol, triethylene glycol, pentaerythritol, tris (hydroxyethyl) iso cyanurate, N, N-bis (hydroxyethyl) oxalic acid diamide, 3-thiaundecanol, 3-thiapentadeca nol, trimethylhexanediol, trimethylolpropane, 4-hydroxymethyl-1-phosphate-2,6,7-trioxabi cyclo [2.2.2] octane.  
• 1.14. Esters of β- (5-tert-butyl-4-hydroxy-3-methylphenyl) -propionic acid with or without polyhydric alcohols, such as. With methanol, ethanol, n-octanol, i-octanol, octade canol, 1,6-hexanediol, 1,9-nonanediol, ethylene glycol, 1,2-propanediol, neopentyl glycol, Thiodiethylene glycol, diethylene glycol, triethylene glycol, pentaerythritol, tris (hydroxy ethyl) isocyanurate, N, N'-bis (hydroxyethyl) oxalic acid diamide, 3-thiaundecanol, 3-thia pentadecanol, trimethylhexanediol, trimethylolpropane, 4-hydroxymethyl-1-phosphate 2,6,7-trioxabicyclo [2.2.2] octane.
• 1.15. Esters of β- (3,5-dicyclohexyl-4-hydroxyphenyl) propionic acid with one or more valent alcohols, such as. With methanol, ethanol, octanol, octadecanol, 1,6-hexanedi ol, 1,9-nonanediol, ethylene glycol, 1,2-propanediol, neopentyl glycol, thiodiethylene glycol, Diethylene glycol, triethylene glycol, pentaerythritol, tris (hydroxyethyl) isocyanurate, N, N'- Bis (hydroxyethyl) oxalic acid diamide, 3-thiaundecanol, 3-thiapentadecanol, trimethyl hexanediol, trimethylolpropane, 4-hydroxymethyl-1-phospha-2,6,7-trioxabicyclo- [2.2.2] octane.
• 16.1. Esters of 3,5-di-tert-butyl-4-hydroxyphenylacetic acid with mono- or polyvalent ones Alcohols, such as. With methanol, ethanol, octanol, octadecanol, 1,6-hexanediol, 1,9-nonanediol, ethylene glycol, 1,2-propanediol, neopentyl glycol, thiodiethylene glycol, diethy glycol, triethylene glycol, pentaerythritol, tris (hydroxyethyl) isocyanurate, N, N'-bis- (hydroxyethyl) oxalic acid diamide, 3-thiaundecanol, 3-thiapentadecanol, trimethylhexane diol, trimethylolpropane, 4-hydroxymethyl-1-phospha-2,6,7-trioxabicyclo [2.2.2] octane.
• 1.17. Amides of (3- (3,5-di-tert-butyl-4-hydroxyphenyl) -propionic acid, such as N, N'-bis- (3,5-di-tert-butyl-4-hydroxyphenylpropionyl) hexamethylenediamine, N, N'-bis (3,5-di-tert-butyl) butyl-4-hydroxyphenylpropionyl) -trimethylenediamine, N, N'-bis (3,5-di-tert-butyl-4-) hydroxyphenylpropionyl) hydrazine.
• 1.18. Ascorbic acid (vitamin C).
• 19.1. Amine antioxidants, such as. N, N'-di-isopropyl-p-phenylenediamine, N, N'- Di-sec-butyl-p-phenylenediamine, N, N'-bis (1,4-dimethylpentyl) -p-phenylenediamine, N, N'- Bis (1-ethyl-3-methyl-pentyl) -p-phenylenediamine, N, N'-bis (1-methyl-heptyl) -p-phenylene diamine, N, N'-dicyclohexyl-p-phenylenediamine, N, N'-diphenyl-p-phenylenediamine, N, N'- Di- (naphthyl-2) -p-phenylenediamine-N-isopropyl-N'-phenyl-p-phenylenediamine, N- (1,3-di  methyl-butyl) -N'-phenyl-p-phenylenediamine, N- (1-methyl-heptyl) -N'-phenyl-p-phenylene diamine, N-cyclohexyl-N'-phenyl-p-phenylenediamine, 4- (p-toluene-sulfonamido) -diphenyl amine, N, N'-dimethyl-N, N'-di-sec-butyl-p-phenylenediamine, diphenylamine, N-allyldiphe nylamine, 4-isopropoxy-diphenylamine, N-phenyl-1-naphthylamine, N- (4-tert-octylphenyl) - 1-naphthylamine, N-phenyl-2-naphthylamine, octylated diphenylamine, e.g. P, p'-di-tertiary octyldiphenylamine, 4-n-butylaminophenol, 4-butyrylamino-phenol, 4-nonanoylamino phenol, 4-dodecanoylamino-phenol, 4-octadecanoylamino-phenol, di- (4-methoxyphe nyl) amine, 2,6-di-tert-butyl-4-dimethylamino-methyl-phenol, 2,4'-diamino-diphenyl methane, 4,4'-diamino-diphenylmethane, N, N, N ', N'-tetramethyl-4,4'-diamino-diphenyl methane, 1,2-di - [(2-methyl-phenyl) -amino] -ethane, 1,2-di- (phenylamino) -propane, (o- Tolyl) -biguanide, di- [4- (1 ', 3'-dimethyl-butyl) -phenyl] amine, tert-octylated N-phenyl-1-ol naphthylamine, mixture of mono- and dialkylated tert-butyl / tert-octyldiphenylamines, Mixture of mono- and dialkylated nonyldiphenylamines, mixture of mono- and di alkylated dodecyldiphenylamines, mixture of mono- and dialkylated isopropyl / iso hexyl-diphenylamines, mixtures of mono- and dialkylated tert-butyldiphenylamines, 2,3-dihydro-3,3-dimethyl-4H-1,4-benzothiazine, phenothiazine, mixture of mono- and di alkylated tert-butyl / tert-octyl-phenothiazines, mixture of mono- and dialkylated tert-octyl-phenothiazines, N-allylphenothiazine, N, N, N ', N'-tetraphenyl-1,4-diaminobut- 2-ene, N, N-bis (2,2,6,6-tetramethyl-piperidin-4-yl-hexamethylenediamine, bis (2,2,6,6-tetra methylpiperidin-4-yl) sebacate, 2,2,6,6-tetramethylpiperidin-4-one, 2,2,6,6-tetramethylpi piperidin-4-ol.

2. UV absorber and sunscreen

• 2.1. 2- (2'-hydroxyphenyl) benzotriazoles, such as. B. 2- (2'-hydroxy-5'-methylphenyl) -ben zotriazole, 2- (3 ', 5'-di-tert-butyl-2'-hydroxyphenyl) benzotriazole, 2- (5'-tert-butyl-2'-hy droxyphenyl) benzotriazole, 2- (2'-hydroxy-5 '- (1,1,3,3-tetramethylbutyl) phenyl) benzotria zol, 2- (3 ', 5'-di-tert-butyl-2'-hydroxyphenyl) -5-chloro-benzotriazole, 2- (3'-tert-butyl-2'hy droxy-5'-methylphenyl) -5-chloro-benzotriazole, 2- (3'-sec-butyl-5'-tert-butyl-2'-hydroxy phenyl) benzotriazole, 2- (2'-hydroxy-4'-octoxyphenyl) benzotriazole, 2- (3 ', 5'-di-tert-butyl) amyl-2'-hydroxyphenyl) benzotriazole, 2- (3 ', 5'-bis (α, α-dimethylbenzyl) -2'-hydroxyphe nyl) benzotriazole, mixture of 2- (3'-tert-butyl-2'-hydroxy-5 '- (2-octyloxycarbonylethyl) - phenyl) -5-chloro-benzotriazole, 2- (3'-tert-butyl-5 '- [2- (2-ethylhexyloxy) -carbonylethyl] -2'- hydroxyphenyl) -5-chloro-benzotriazole, 2- (3'-tert-butyl-2'-hydroxy-5 '- (2-methoxycarbonyl ethyl) phenyl) -5-chloro-benzotriazole, 2- (3-tert-butyl-2'-hydroxy-5 '- (2-methoxycarbonyl ethyl) phenyl) benzotriazole, 2- (3'-tert-butyl-2'-hydroxy-5 '- (2-octyloxycarbonylethyl) phe  nyl) benzotriazole, 2- (3'-tert-butyl-5 '- [2- (2-ethylhexyloxy) carbonylethyl] -2'-hydroxyphenyl nyl) benzotriazole, 2- (3'-dodecyl-2'-hydroxy-5'-methylphenyl) benzotriazole, and 2- (3'- tert -Butyl 2'-hydroxy-5 '- (2-isooctyloxycarbonylethyl) phenylbenzotriazole, 2,2'-methylene bis [4- (1,1,3,3-tetramethylbutyl) -6-benzotriazol-2-yl-phenol]; Transesterification product of 2- [3'-tert-Butyl-5 '- (2-methoxycarbonylethyl) -2'-hydroxy-phenyl] -benzotriazole with polyethyl Glycol 300; [R-CH₂CH₂-COO (CH₂) ₃] ₂- with R = 3'-tert-butyl-4'-hydroxy-5'-2H-benzo triazol-2-yl-phenyl.
• 2.2. 2-hydroxybenzophenones, such as. As the 4-hydroxy, 4-methoxy, 4-octoxy, 4-decyl oxy, 4-dodecyloxy, 4-benzyloxy, 4,2 ', 4'-trihydroxy, 2'-hydroxy-4,4'-dimethoxy Derivative.
• 2.3. Esters of optionally substituted benzoic acids, such as. B. 4-tert-butyl-phenyl salicylate, phenyl salicylate, octylphenyl salicylate, dibenzoylresorcinol, bis (4-tert-butyl benzoyl) resorcinol, benzoylresorcinol, 3,5-di-tert-butyl-4-hydroxybenzoic acid 2,4-di-tert-butyl butylphenyl ester, 3,5-di-tert-butyl-4-hydroxybenzoic acid hexadecyl ester, 3,5-di-tert-butyl butyl-4-hydroxybenzoic acid octadecyl ester, 3,5-di-tert-butyl-4-hydroxybenzoic acid-2 methyl-4,6-di-tert-butylphenyl ester.
• 2.4. Acrylates, such as. B. α-cyano-β, β-diphenylacrylic acid ethyl ester or isooctyl ester, α-Carbomethoxy-cinnamic acid methyl ester, α-cyano-β-methyl-p-methoxycinnamic acid methyl ester or butyl ester, α-carbomethoxy-p-methoxycinnamic acid methyl ester, N- (β-Carbo methoxy-β-cyanovinyl) -2-methyl-indoline.
• 2.5. Nickel compounds, such as. B. nickel complexes of 2,2'-thio-bis [4- (1,1,3,3-tetra methylbutyl) -phenol], such as the 1: 1 or the 1: 2 complex, optionally with additional ligands, such as n-butylamine, triethanolamine or N-cyclohexyl-diethanolamine, Nickel dibutyldithiocarbamate, nickel salts of 4-hydroxy-3,5-di-tert-butylbenzylphos phonic acid monoalkyl esters, such as of the methyl or ethyl ester, nickel complexes of ketone oximes, such as 2-hydroxy-4-methylphenyl undecylketoxime, nickel complexes of 1-phenyl-4-lauroyl-5-hydroxy-pyrazole, optionally with additional ligands.
• 2.6. Sterically hindered amines, such as. Bis (2,2,6,6-tetramethylpiperidin-4-yl) sebacate, Bis (2,2,6,6-tetramethylpiperidin-4-yl) succinate, bis (1,2,2,6,6-pentamethylpiperidine-4- yl) sebacate, bis (1-octyloxy-2,2,6,6-tetramethylpiperidin-4-yl) sebacate, n-butyl-3,5-di- tert-butyl-4-hydroxybenzyl malonic acid bis (1,2,2,6,6-pentamethylpipenediyl) ester, Kon  condensation product of 1-hydroxyethyl-2,2,6,6-tetramethyl-4-hydroxypiperidine and Bern tartaric acid, condensation product of N, N'-bis (2,2,6,6-tetramethyl-4-piperidyl) hexa methylenediamine and 4-tert-octylamino-2,6-dichloro-1,3,5-s-triazine, tris (2,2,6,6-tetra methyl-4-piperidyl) nitrilotriacetate, tetrakis (2,2,6,6-tetramethyl-4-piperidyl) -1,2,3,4- butanetetraoate, 1,1 '- (1,2-ethanediyl) -bis (3,3,5,5-tetramethylpiperazinone), 4-benzoyl- 2,2,6,6-tetramethylpiperidine, 4-stearyloxy-2,2,6,6-tetramethylpiperidine, bis (1,2,2,6,6- pentamethylpiperidyl) -2-n-butyl-2- (2-hydroxy-3,5-di-tert-butylbenzyl) malonate, 3-n- Octyl-7,7,9,9-tetramethyl-1,3,8-triazaspiro [4.5] decane-2,4-dione, bis (1-octyloxy-2,2,6,6- tetramethylpiperidyl) sebacate, bis (1-octyloxy-2,2,6,6-tetramethylpiperidyl) succinate, Kon condensation product of N, N'-bis (2,2,6,6-tetramethyl-4-piperidyl) hexamethylenediamine and 4-morpholino-2,6-dichloro-1,3,5-triazine, condensation product of 2-chloro-4,6-di- (4-n-) butylamino-2,2,6,6-tetramethylpiperidyl) -1,3,5-triazine and 1,2-bis (3-aminopropylamino) - ethane, condensation product of 2-chloro-4,6-di- (4-n-butylamino-1,2,2,6,6-pentamethyl piperidyl) -1,3,5-triazine and 1,2-bis (3-aminopropylamino) ethane, 8-acetyl-3-dodecyl 7,7,9,9-tetramethyl-1,3,8-triazaspiro [4.5] decane-2,4-dione, 3-dodecyl-1- (2,2,6,6-tetra methyl-4-piperidyl) pyrrolidine-2,5-dione, 3-dodecyl-1- (1,2,2,6,6-pentamethyl-4-piperidyl) - pyrrolidine-2,5-dione, mixture of 4-hexadecyloxy and 4-stearyloxy-2,2,6,6-tetramethyl piperidine, condensation product of N, N'-bis (2,2,6,6-tetramethyl-4-piperidyl) hexamethylene lendiamine and 4-cyclohexylamino-2,6-dichloro-1,3,5-triazine, condensation product 1,2-bis (3-aminopropylamino) ethane and 2,4,6-trichloro-1,3,5-triazine and 4-butylamino 2,2,6,6-tetramethylpiperidine (CAS Reg. No. [136504-96-6]), N- (2,2,6,6-tetramethyl-4-pi peridyl) -n-dodecylsuccinimide, N- (1,2,2,6,6-pentamethyl-4-piperidyl) -n-dodecylsuccin imide, 2-undecyl-7,7,9,9-tetramethyl-1-oxa-3,8-diaza-4-oxo-spiro [4,5] decane, - Reaction 7,7,9,9-tetramethyl-2-cycloundecyl-1-oxa-3,8-diaza-4-oxospiro [4,5] de-can and epichlorohydrin.
• 2.7. Oxidesäurediamide, such as. 4,4'-dioctyloxy-oxanilide, 2,2'-diethoxy-oxanilide, 2,2'- Di-octyloxy-5,5'-di-tert-butyl-oxanilide, 2,2'-di-dodecyloxy-5,5'-di-tert-butyl-oxanilide, 2- Ethoxy-2'-ethyl-oxanilide, N, N'-bis (3-dimethylaminopropyl) oxalamide, 2-ethoxy-5-tert-butyl Butyl-2'-ethyloxanilide and its mixture with 2-ethoxy-2'-ethyl-5,4'-di-tert-butyl-oxani lid, mixtures of o and p-methoxy and of o and p-ethoxy-di-substituted oxani liden.
• 2.8. 2- (2-hydroxyphenyl) -1,3,5-triazines, such as. B. 2,4,6-tris (2-hydroxy-4-octyloxyphe nyl) -1,3,5-triazine, 2- (2-hydroxy-4-octyloxyphenyl) -4,6-bis (2,4-dimethylphenyl) -1,3,5-tri- azine, 2- (2,4-dihydroxyphenyl) -4,6-bis (2,4-dimethylphenyl) -1,3,5-triazine, 2,4-bis (2-  hydroxy-4-propyloxyphenyl) -6- (2,4-dimethylphenyl) -1,3,5-triazine, 2- (2-hydroxy-4-octyl oxyphenyl) -4,6-bis (4-methylphenyl) -1,3,5-triazine, 2- (2-hydroxy-4-dodecyloxyphenyl) - 4,6-bis (2,4-dimethylphenyl) -1,3,5-triazine, 2- (2-hydroxy-4-tridecyloxyphenyl) -4,6-bis- (2,4-dimethylphenyl) -1,3,5-triazine, 2- [2-hydroxy-4- (2-hydroxy-3-butyloxy-propyloxy) - phenyl] -4,6-bis (2,4-dimethylphenyl) -1,3,5-triazine, 2- [2-hydroxy-4- (2-hydroxy-3-octyl oxy-propyloxy) phenyl] -4,6-bis (2,4-dimethylphenyl) -1,3,5-triazine, 2- [4- (dodecyloxy / tride cyloxy-2-hydroxypropoxy) -2-hydroxy-phenyl] -4,6-bis (2,4-dimethylpheny l) -1,3,5-triazine, 2- [2-hydroxy-4- (2-hydroxy-3-dodecyloxy-propoxy) phenyl] -4,6-bis (2,4-d-imethylphenyl) - 1,3,5-triazine, 2- (2-hydroxy-4-hexyloxy) phenyl-4,6-diphenyl-1,3,5-triazine, 2- (2-hydroxy) 4-methoxyphenyl) -4,6-diphenyl-1,3,5-triazine, 2,4,6-tris [2-hydroxy-4- (3-butoxy-2- hydroxy-propoxy) phenyl] -1,3,5-triazine, 2- (2-hydroxyphenyl) -4- (4-methoxyphenyl) -6- phenyl-1,3,5-triazine.
• 3. Metal deactivators, such as. N, N'-diphenyloxalic diamide, N-salicylal-N'-salicy lohydrazine, N, N'-bis (salicyloyl) hydrazine, N, N'-bis (3,5-di-tert-butyl-4-hydroxyphenyl propionyl) hydrazine, 3-salicyloylamino-1,2,4-triazole, bis (benzylidene) -oxalic acid hydrazide, oxanilide, isophthalic dihydrazide, sebacic acid bis-phenylhydrazide, N, N'-di acetyl-adipic acid dihydrazide, N, N'-bis-salicyloyl-oxalic acid dihydrazide, N, N'-bis-sali cyloyl-thiopropionic dihydrazide.
• 4. phosphites and phosphonites, such as. B. triphenyl phosphite, Diphenylalkylphosphite, Phe nyldialkyl phosphites, tris (nonylphenyl) phosphite, trilauryl phosphite, trioctadecyl phosphite, Distearyl pentaerythritol diphosphite, tris (2,4-di-tert-butylphenyl) phosphite, diisodecylpenta erythritol diphosphite, bis (2,4-di-tert-butylphenyl) pentaerythritol diphosphite, bis (2,6-di-tert-butyl) butyl-4-methylphenyl) -pentaerythritol diphosphite, bis-isodecyloxy-pentaerythritol diphosphite, Bis (2,4-di-tert-butyl-6-methylphenyl) pentaerythritol diphosphite, bis (2,4,6-tri-tert-butylphe nyl) -pentaerythritol diphosphite, tristearyl sorbitol triphosphite, tetrakis (2,4-di-tert-butylphe nyl) -4,4'-biphenylene-diphosphonite, 6-isooctyloxy-2,4,8,10-tetra-tert-butyl-12H-di benz [d, g] -1,3,2-dioxaphosphocine, 6-fluoro-2,4,8,10-tetra-tert-butyl-12-methyl-dibenzoyl [d, g] -1,3,2-dioxaphosphocine, bis (2,4-di-tert-butyl-6-methylphenyl) -methylphosphite, bis- (2,4-di-tert-butyl-6-methylphenyl) -ethylphosphit.
• 5. Hydroxylamines such. N, N-dibenzylhydroxylamine, N, N-diethylhydroxylamine, N, N- Dioctylhydroxylamine, N, N-dilaurylhydroxylamine, N, N-ditetradecylhydroxylamine, N, N- Dihexadecylhydroxylamine, N, N-dioctadecylhydroxylamine, N-hexadecyl-N-octadecyl hydroxylamine, N-heptadecyl-N-octadecylhydroxylamine, N, N-dialkylhydroxylamine  hydrogenated tallow fatty amines.
• 6. Nitrone like z. N-benzyl-alpha-phenyl-nitron, N-ethyl-alpha-methyl-nitron, N-Oc tyl-alpha-heptyl-nitron, N-lauryl-alpha-undecyl-nitron, N-tetradecyl-alpha-tridecyl nitron, N-hexadecyl-alpha-pentadecyl-nitron, N-octadecyl-alpha-heptadecyl-nitron, N- Hexadecyl-alpha-heptadecyl-nitron, N-octadecyl-alpha-pentadecyl-nitron, N-heptade cyl-alpha-heptadecyl-nitron, N-octadecyl-alpha-hexadecyl-nitron, nitrones derived from N, N-dialkylhydroxylamines prepared from hydrogenated tallow fatty amines.
• 7. thiosynergists such. For example, thiodipropionic acid di-lauryl ester or thiodipropionic acid di-octyl ester.
• 8. peroxide-destroying compounds, such as. B. esters of β-thio-dipropionic acid, for example example, the lauryl, stearyl, myristyl or tridecyl ester, mercaptobenzimidazole, the Zinc salt of 2-mercaptobenzimidazole, zinc dibutyl dithiocarbamate, dioctadecyl disulfide, Pentaerythritol tetrakis (β-dodecylmercapto) propionate.
• 9. polyamide stabilizers, such as. As copper salts in combination with iodides and / or Phosphorus compounds and salts of divalent manganese.
• 10. Basic co-stabilizers, such as. Melamine, polyvinylpyrrolidone, dicyandiamide, Triallyl cyanurate, urea derivatives, hydrazine derivatives, amines, polyamides, polyure thane, alkali and alkaline earth salts of higher fatty acids, for example calcium stearate, Zn stearate, Mg behenate, Mg stearate, Na ricinoleate, K palmitate, antimony catechinate or tin catechinate.
• 11. nucleating agents, such as. As inorganic substances such. As talc, metal oxides such as Titanium dioxide or magnesium oxide, phosphates, carbonates or sulfates of preferably alkaline earth metals; organic compounds such as mono- or polycarboxylic acids as well their salts such. For example, 4-tert-butylbenzoic acid, adipic acid, diphenylacetic acid, sodium succinate or sodium benzoate; polymeric compounds such. B. ionic copolymers ( "Ionomers").
• 12. Fillers and reinforcing agents, such as. Calcium carbonate, silicates, glass fibers, Glass beads, asbestos, talc, kaolin, mica, barium sulfate, metal oxides and hydroxides, Carbon black, graphite, wood flour and flours or fibers of other natural products, synthetic  Fibers.
• 13. Other additives, such. As plasticizers, lubricants, emulsifiers, pigments, Rheo logieadditive, catalysts, leveling agents, optical brighteners, flame retardants, Antistatic agents, propellants.
• 14. Benzofuranone or indolinones, such as. In US-A-4 325 863, US-A-4 338 244, US-A-5 175 312, US-A-5 216 052, US-A-5 252 643, DE-A-43 16 611, DE-A-43 16 622, DE-A-43 16 876, EP-A-0 589 839 or EP-A-0 591 102, or 3- [4- (2-Ace toxyethoxy) phenyl] -5,7-di-tert-butylbenzofuran-2-one, 5,7-di-tert-butyl-3- [4- (2-stearoyl oxyethoxy) phenyl] benzofuran-2-one, 3,3'-bis [5,7-di-tert-butyl-3- (4- [2-hydroxyethoxy] - phenyl) -benzofuran-2-one], 5,7-di-tert-butyl-3- (4-ethoxyphenyl) -benzofuran-2-one, 3- (4- Acetoxy-3,5-dimethylphenyl) -5,7-di-tert-butylbenzofuran-2-one, 3- (3,5-dimethyl-4-piva loyloxy-phenyl) -5,7-di-tert-butyl-benzofuran-2-one.

Of particular importance is the addition of sterically hindered amines (Section 2.6 the above list), since these with the modified polymers a particular result in effective light stabilization.

If the additives are stabilizers, they are preferably used in an amount of a total of 0.05 to 5 wt .-% added.

Another embodiment of the invention is that in addition to a compound of Formula (I) incorporates a further stabilizer in the polymer. Of special interest is the additional incorporation of a sterically hindered amine. Depending on whether you are one hindered amine containing an ethylenically unsaturated group or a contains other functional group, the incorporation by copolymerization or Copolycondensation or Copolyaddition or by reaction with a polymer, the contains appropriate functional groups done.

Sterically hindered amines containing ethylenically unsaturated groups and invented According to the invention are suitable for copolymerization, z. In US-A-3,705,166 described acrylic and methacrylic acid derivatives of 2,2,6,6-tetramethylpiperidine as well as its N-alkyl and N-alkoxy derivatives. Other copolymerizable derivatives of Tetramethylpiperidines are described in US-A-4,210,612 and in EP-A-389,420.  

Sterically hindered amines which can react with functional polymers are e.g. B. those containing hydroxyl groups, such as. The 2,2,6,6-tetramethylpiperidinol-4, 1,2,2,6,6-pentamethylpiperidinol-4, 1-hydroxyethyl-2,2,6,6-tetramethyl piperidinol-4 or those described in US-A-4 087 404 and in EP-A 389,419 Links; or those containing amino groups, such as. B. the 4-amino-2,2,6,6-tetramethylpiperidine or those described in US-A-3,904,581 4-aminopiperidines.

The incorporation of such sterically hindered amines can be done simultaneously with the incorporation of the Triazines of the formula (I) or before or after happen. The ones used for this Procedures are the same as for the incorporation of the triazines. Further details can be found in the examples below.

In addition to the triazine compound of the formula (I), a sterically hindered amine in the polymer incorporated, the latter is preferably used in an amount which is 0.1 to 15% by weight of the modified polymer. The same applies to an invent The copolymer according to the invention containing units of the formula Id.

The polymers modified according to the invention can be used for the usual purpose forms of polymers are used, such as. B. as moldings, pipes, plates, films, Fibers, casting resins, adhesives or coatings. Preferably, they are used as Binders for paints, both for pigmented and unpigmented paints.

Furthermore, the compounds of the formula (I) or (Id) and the modified Polymers as described above as stabilizers for organic Materials, mainly for polymers used. For this one uses as modified polymers preferably those containing at least 5%, for example 5-50%, a compound of formula (I) or (Id) in built-in form. The invention suitable stabilizers are preferably used in an amount of from 0.01 to 10% by weight, particularly 0.05 to 5 wt .-% used (based on the organic to be stabilized Material). The compounds of the invention can be used to stabilize organic materials such. As oils, fats, waxes, cosmetics, paints or Coatings are used, in particular for stabilizing organic Polymers. Examples of polymers that can be so stabilized are the following:

• 1. Polymers of monoolefins and diolefins, for example polypropylene, polyisobutylene,  Polybutene-1, poly-4-methylpentene-1, polyisoprene or polybutadiene and polymers of cycloolefins such as. From cyclopentene or norbornene; furthermore polyethylene (the ge if necessary can be networked), z. High density polyethylene (HDPE), polyethylene ho density and high molecular weight (HDPE-HMW), high-density polyethylene and ultrahigh-density Molecular weight (HDPE-UHMW), medium density polyethylene (MDPE), low-density polyethylene Density (LDPE), linear low density polyethylene (LLDPE), branched polyethylene low density (VLDPE).

Polyolefins, d. H. Polymers of monoolefins, as exemplified in the above Paragraph, especially polyethylene and polypropylene, may be different Processes are prepared, in particular by the following methods:

• a) radical (usually at high pressure and high temperature).
• b) by means of catalyst, wherein the catalyst usually one or more metals Group IVb, Vb, VIb or VIII contains. These metals usually own one or more ligands such as oxides, halides, alcoholates, esters, ethers, Amines, alkyls, alkenyls and / or aryls that are either π- or σ-coordinated can. These metal complexes may be free or supported on supports as in For example, on activated magnesium chloride, titanium (III) chloride, alumina or silica. These catalysts can dissolve in the polymerization medium be insoluble or insoluble. The catalysts can be used as such in the Polymerisa tion, or other activators can be used, as in For example, metal alkyls, metal hydrides, metal alkyl halides, metal alkyl oxides or metal alkyloxanes, where the metals are elements of groups Ia, IIa and / or IIIa. The activators can be used, for example, with further ester, Ether, amine or silyl ether groups may be modified. This catalysty stems are commonly referred to as Phillips, Standard Oil Indiana, Ziegler (-Natta) TNZ (DuPont), metallocene or single site catalysts (SSC).
• 2. mixtures of the polymers mentioned under 1), for. B. mixtures of polypropylene with Polyisobutylene, polypropylene with polyethylene (eg PP / HDPE, PP / LDPE) and Mischun various types of polyethylene (eg LDPE / HDPE).
• 3. Copolymers of monoolefins and diolefins with each other or with other vinyl mono mers, such as B. Ethylene Propylene Copolymers, Linear Low Density Polyethylene (LLDPE)  and mixtures thereof with low density polyethylene (LDPE), propylene Butene-1 copolymers, propylene-isobutylene copolymers, ethylene-butene-1 copolymers, Ethylene-hexene copolymers, ethylene-methylpentene copolymers, ethylene-heptene-co polymers, ethylene-octene copolymers, propylene-butadiene copolymers, isobutylene-iso pren copolymers, ethylene-alkyl acrylate copolymers, ethylene-alkyl methacrylate copoly mers, ethylene-vinyl acetate copolymers and their copolymers with carbon monoxide, or ethylene-acrylic acid copolymers and their salts (ionomers), as well as terpolymers of ethylene with propylene and a diene, such as hexadiene, dicyclopentadiene or ethyli dennorbornen; furthermore, mixtures of such copolymers with one another and with 1) ge called polymers, eg. As polypropylene / ethylene-propylene copolymers, LDPE / ethylene Vinyl acetate copolymers, LDPE / Ethyfrn-acrylic acid copolymers LLDPE / ethylene-vinyl acetate copolymers, LLDPE / ethylene-acrylic acid copolymers and alternating or statis table constructed polyalkylene / carbon monoxide copolymers and mixtures thereof with other polymers such. B. polyamides.
• 4. Hydrocarbon resins (eg C₅-C₉) including hydrogenated modifications thereof (eg Tackifier resins) and blends of polyalkylenes and starch.
• 5. polystyrene, poly (p-methylstyrene), poly (α-methylstyrene).
• 6. Copolymers of styrene or α-methylstyrene with dienes or acrylic derivatives, such as. B. Styrene-butadiene, styrene-acrylonitrile, styrene-alkyl methacrylate, styrene-butadiene-alkylacry lat and methacrylate, styrene-maleic anhydride, styrene-acrylonitrile-methyl acrylate; Mixtures of high impact strength from styrene copolymers and another poly mer, such as As a polyacrylate, a diene polymer or an ethylene-propylene Diene terpolymer; and block copolymers of styrene, such as. Styrene-butadiene-styrene, Styrene-isoprene-styrene, styrene-ethylene / butylene-styrene or styrene-ethylene / propyne len-styrene.
• 7. graft copolymers of styrene or α-methylstyrene, such as. Styrene on polybutadiene, Styrene on polybutadiene-styrene or polybutadiene-acrylonitrile copolymers, styrene and Acrylonitrile (or methacrylonitrile) on polybutadiene, styrene, acrylonitrile and methylmeth acrylate on polybutadiene; Styrene and maleic anhydride on polybutadiene; Styrene, acrylic nitrile and maleic anhydride or maleimide on polybutadiene, styrene and Maleimide on polybutadiene, styrene and alkyl acrylates or alkyl methacrylates Polybutadiene, styrene and acrylonitrile on ethylene-propylene-diene terpolymers, styrene and  Acrylonitrile on polyalkyl acrylates or polyalkyl methacrylates, styrene and acrylonitrile Acrylate-butadiene copolymers, and mixtures thereof with the mentioned under 6) Co polymers, such as. B. known as so-called ABS, MBS, ASA or AES polymers are.
• 8. Halogen-containing polymers, such as. As polychloroprene, chlorinated rubber, chlorinated and brominated copolymer of isobutylene-isoprene (halobutyl rubber), chlorinated or chlorosulfonated polyethylene, copolymers of ethylene and chlorinated ethylene, Epi chlorohydrin homo- and copolymers, in particular polymers of halogen-containing vinyl connections, such. As polyvinyl chloride, polyvinylidene chloride, polyvinyl fluoride, Polyvi nylidenfluorid; and their copolymers, such as vinyl chloride-vinylidene chloride, vinyl chloride Ride vinyl acetate or vinylidene chloride vinyl acetate.
• 9. Polymers derived from α, β-unsaturated acids and their derivatives, such as Polyacrylates and polymethacrylates, polymethyl impact-modified with butyl acrylate methacrylates, polyacrylamides and polyacrylonitriles.
• 10. Copolymers of the monomers mentioned under 9) with each other or with other unge saturated monomers such. For example, acrylonitrile-butadiene copolymers, acrylonitrile alkylacry lat copolymers, acrylonitrile-alkoxyalkyl acrylate copolymers, acrylonitrile-vinyl halide Copolymers or acrylonitrile-alkyl methacrylate-butadiene terpolymers.
• 11. Polymers derived from unsaturated alcohols and amines or their acylderiva derived or acetals, such as polyvinyl alcohol, polyvinyl acetate, stearate, benzoate, maleate, polyvinyl butyral, polyallyl phthalate, polyallylmelamine; and their copolymers with olefins mentioned in point 1.
• 12. Homopolymers and copolymers of cyclic ethers, such as polyalkylene glycols, polyethylene oxide, polypropylene oxide or their copolymers with bisglycidyl ethers.
• 13. Polyacetals, such as polyoxymethylene, as well as those polyoxymethylenes, the Comono mere, such. For example, ethylene oxide; Polyacetals made with thermoplastic polyurethane NEN, acrylates or MBS are modified.
• 14. Polyphenylene oxides and sulfides and their mixtures with styrene polymers or Polyamides.  
• 15. Polyurethanes which are derived from polyethers, polyesters and polybutadienes Hydroxyl groups on the one hand and aliphatic or aromatic polyisocyanates dererseits, as well as their precursors.
• 16. polyamides and copolyamides derived from diamines and dicarboxylic acids and / or derive from aminocarboxylic acids or the corresponding lactams, such as polyamide 4, Polyamide 6, polyamide 6/6, 6/10, 6/9, 6/12, 4/6, 12/12, polyamide 11, polyamide 12, aromati typical polyamides starting from m-xylene, diamine and adipic acid; Polyamides, manufactured from hexamethylenediamine and isophthalic and / or terephthalic acid and optionally one Elastomer as modifier, z. B. poly-2,4,4-trimethylhexamethylene terephthalamide or Poly-m-phenylene isophthalamide. Block copolymers of the aforementioned polyamides with polyolefins, olefin copolymers, ionomers or chemically bonded or ge grafted elastomers; or with polyethers, such as. B. with polyethylene glycol, polypropylene glycol or polytetramethylene glycol. Further modified with EPDM or ABS poly amides or copolyamides; as well as condensed polyamides during processing ( "RIM polyamide systems").
• 17. Polyureas, polyimides, polyamide-imides, polyetherimides, polyesterimides, polyhy dantoine and polybenzimidazoles.
• 18. Polyesters derived from dicarboxylic acids and dialcohols and / or hydroxy derived carboxylic acids or the corresponding lactones, such as polyethylene terephthalate, Polybutylene terephthalate, poly-1,4-dimethylolcyclohexane terephthalate, polyhydroxybenzo ate, as well as block polyether esters derived from hydroxyl-terminated polyethers th; also with polycarbonates or MBS modified polyester.
• 19. polycarbonates and polyestercarbonates.
• 20. polysulfones, polyethersulfones and polyetherketones.
• 21. Crosslinked polymers derived from aldehydes on the one hand and phenols, urea or Derive melamine on the other hand, such as phenol-formaldehyde, urea-formaldehyde and Melamine-formaldehyde resins.
• 22. Drying and non-drying alkyd resins.  
• 23. Unsaturated polyester resins derived from copolyesters of saturated and unsaturated di carboxylic acids with polyhydric alcohols, as well as vinyl compounds as Vernetzungsmit derive tel, as well as their halogen-containing, flame-retardant modifications.
• 24. Crosslinkable acrylic resins derived from substituted acrylic acid esters, such as. B. of epoxy acrylates, urethane acrylates or polyester acrylates.
• 25. Alkyd resins, polyester resins and acrylate resins containing melamine resins, urea resins zen, isocyanates, isocyanurates, polyisocyanates or epoxy resins are crosslinked.
• 26. Crosslinked epoxy resins, which differ from aliphatic, cycloaliphatic, heterocycli derive or aromatic glycidyl compounds, z. B. Products of bisphenol-A- diglycidyl ethers, bisphenol-F-diglycidyl ethers, by means of conventional hardeners such. B. An hydrides or amines are crosslinked with or without accelerators.
• 27. Natural polymers, such as cellulose, natural rubber, gelatin, and their polymer homologous chemically modified derivatives, such as cellulose acetates, propionates and butyric rate, or the cellulose ethers, such as methylcellulose; as well as rosin resins and Deri vate.
• 28. mixtures (polyblends) of the aforementioned polymers, such as. PP / EPDM, poly amid / EPDM or ABS, PVC / EVA, PVC / ABS, PVC / MBS, PC / ABS, PBTP / ABS, PC / ASA, PCIPBT, PVC / CPE, PVC / Acrylate, POM / Thermoplastic PUR, PC / Thermo plastic PUR, POM / acrylate, POM / MBS, PPO / HIPS, PPO / PA 6.6 and copolymers, PA / HDPE, PA / PP, PA / PPO, PBT / PC / ABS or PBT / PET / PC.

The invention therefore also relates to a process for stabilizing organic Material against damage from light, oxygen and / or heat, thereby characterized in that this is a stabilizer as a compound of formula (I) or a Polymer added, which consists of monomers of the formula (Id) and optionally further Monomers is built, as well as the use of these compounds for stabilizing of organic material.

The amount of stabilizer to be used depends on the one to be stabilized organic material and the intended use of the stabilized material. in the  In general, the composition according to the invention contains up to 100 parts by weight Stabilizing material 0.01 to 15, especially 0.05 to 10, and especially 0.1 to 5 parts by weight of the stabilizer.

The incorporation into the organic polymers, for example in the synthetic organic, in particular thermoplastic polymers, by adding the Compounds according to the invention and optionally further additives according to the in the Technique usual methods take place. The incorporation may be appropriate before or during shaping, for example by mixing the powdered Components or by adding the stabilizer to the melt or solution of Polymers, or by applying the dissolved or dispersed compounds on the Polymers, optionally with subsequent evaporation of the solvent. In the case of elastomers, these can also be stabilized as latices. Another Possibility of incorporating the compounds of the invention into polymers in their addition before or during the polymerization of the corresponding monomers or before networking.

The compounds of the invention or mixtures thereof may also be in the form a masterbatch containing these compounds, for example in a concentration of Contains 2.5 to 25 wt .-%, are added to the plastics to be stabilized.

Suitably, the incorporation of the compounds of the invention according to the following Methods are done:

• as emulsion or dispersion (eg to latices or emulsion polymers)
• as a dry mixture during the mixing of additional components or polymer blends
• by direct addition to the processing apparatus (eg extruder, internal mixer etc.)
• - as a solution or melt.

The resulting stabilized polymer compositions can be prepared according to the usual Methods, such. By hot pressing, spinning, extruding or injection molding, in shaped objects are transferred, such. As in fibers, films, tapes, plates, Multi-wall sheets, vessels, pipes and other profiles.

The invention therefore further relates to the use of the polymer according to the invention  composition for producing a molded article.

Also of interest is the use in multilayer systems. Here is a Polymer composition according to the invention with a relatively high content Stabilizer of the formula (I) or the polymer of monomers of the formula (Id) and optionally further monomers, for example 5-15 wt .-%, in a thin layer (10-100 microns) on a molded article of a polymer, the little or none Stabilizer of formula (I) or (Id) contains applied. The application can at the same time done with the shape of the body, z. B. by so-called coextrusion. The application can also be done on the finished molded body, z. B. by lamination with a film or by coating with a solution. The outer one Layer or the outer layers of the finished article have the function of a UV filter that protects the inside of the object against UV light. The outer layer preferably contains 5-15% by weight, in particular 5-10% by weight, of at least one Stabilizer of the formula (I) or (Id).

The use of the polymer composition according to the invention for the preparation of Multilayer systems, wherein the outer layer (s) in a thickness of 10-100 microns from a polymer composition according to the invention, while the inner layer contains little or no stabilizer of formula (I) or (Id), therefore, provides another Subject of the invention.

Of particular interest is the use of a polymer composition according to the invention Composition, wherein the component A is a polycarbonate, for the preparation of Multilayer systems.

The polymers thus stabilized are characterized by high weather resistance all due to high resistance to UV light. You keep it in the outside use their mechanical properties as well as their color and shine for a long time.

The stabilizer may also be a mixture of two or more Ver invention bonds. The compositions of the invention, stabilized coating agents or organic materials, in addition to the stabilizer of formula I or Id contain other stabilizers or other additives, such as. As antioxidants, more Light stabilizers, metal deactivators, phosphites or phosphonites. Examples of this are the above-mentioned antioxidants, light stabilizers and other additives (3.-11.).  

The following examples further describe the subject matter of the invention without restricting it to the examples. Where parts are parts by weight and% by weight; If room temperature is mentioned in an example, it is to be understood as a temperature in the range 20-25 ° C. These specifications apply unless otherwise stated. Numbers directly behind chemical symbols represent indices of the chemical formula, even if they are not subscripted.
The following abbreviations apply:

THF tetrahydrofuran AIBN α, α'-azoisobutyronitrile Section. anhydrous Mp. Melting point or melting range mmHg Torr (1 mmHg = 133.3224 Pa) MALDI Matrix Assisted Laser Desorption Ionization MS Mass spectrometry NMR Nuclear magnetic resonance GC Gas chromatography GPC Gel Permeation Chromatography DSC Differential scan calorimetry Mn Number average molecular weight (unit g / mol) mw Weight average molecular weight (unit g / mole) Tg glass transition temperature

Example 1

Under nitrogen, a mixture of 14.2 g (30 mmol) of 2,4-diphenyl-6- [2-hydroxy-4- (3-n-butoxy-2-hydroxypropoxy) phenyl] 1,3,5-triazine, 3.5 g (38 mmol) Acryloyl chloride, 0.4 g (5 mmol) of pyridine in 100 ml of toluene at 70 ° C for 24 hours heated. After addition of 4.5 g (44 mmol) of triethylamine is added for a further 6 hours Heated to 70 ° C. It is allowed to cool and the solid residue ((CH₃CH₂) ₃N · HCl) is filtered off. The filtrate is evaporated and 17.5 g of the resin-like crude product are obtained. By column chromatography (Kieselgel 60, 230-400 mesh, eluent CH₂Cl₂ / CH₃OH 95/5) gives 12.5 g (79% yield) of 2,4-diphenyl-6- [2-hydroxy-4- (3-n-butoxy-2- acryloyloxy-propoxy-) phenyl-] 1,3,5-triazine (compound 100) as a yellowish resin.

The ¹H-NMR spectrum (CDCl₃, 300 MHz) is in agreement with the desired product.
Elemental analysis for C₃₁ H₃₁N₃O₅ (525.60):
Theory: C: 70.84; H: 5.94; N: 7.99%;
Found: C: 70.80; H: 5.85; N: 8.02%.

example 2

Under nitrogen, a mixture of 14.2 g (30 mmol) 2,4-Diphenyl-6- [2-hydroxy-4- (3-n-butoxy-2-hydroxypropoxy) phenyl] -1,3,5-triazine, 8.0 g (76 mmol) of methacryloyl chloride, 0.4 g (5 mmol) of pyridine in 100 ml of toluene at 80 ° C heated for 48 hours. The excess methacryloyl chloride and the toluene become removed at the Rotavapor. After addition of 100 ml of toluene and 4.5 g (44 mmol) Triethylamine is heated at 75 ° C for 5 hours. It is allowed to cool and filtered solid residue ((CH₃CH₂) ₃N · HCl). The filtrate is evaporated and obtained 18.4 g of the crude product. By column chromatography (Kieselgel 60; 230-400 mesh; Diameter 8 cm, h = 30 cm; Eluent CH₂Cl₂) gives 8.5 g 2,4-diphenyl-6- [2-hydroxy-4- (3-n-butoxy-2-methacryloyloxy-propoxy) p henyl-] 1,3,5- triazine (compound 101) as a yellowish resin.

The ¹H-NMR spectrum (CDCl₃, 300 MHz) is in agreement with the desired product.
Elemental analysis for C₃₂H₃₃N₃O₅ (539.63):
Theory: C: 71.22; H: 6,16; N: 7.79%;
Found: C: 70.42; H: 6.28; N: 7.57%.

Intermediate for example 3 2- [2-hydroxy-4- (11-hydroxy-undecyloxy) -phenyl] -4,6- diphenyl-1,3,5-triazine

A mixture of 170.7 g (0.5 mol) of 2- (2,4-dihydroxyphenyl) -4,6-diphenyl-1,3,5-triazine, 28.1 g (0.5 mol) of powdered potassium hydroxide (Fluka, <85%) in 1000 ml of diglyme (Fluka, 99%) is heated to 80 ° C under nitrogen. To the yellow solution is added 155.4 g (0.6 mol) of 11-bromo-1-undecanol (Fluka, 97%). The mixture is held at 100 ° C for 40 hours. Subsequently, the solid is filtered off hot. The filtrate crystallized on cooling to 0 ° C is washed with hexane and dried at 50 ° C / 70 mmHg. This gives 219.5 g (85.84%) of 2- [2-hydroxy-4- (11-hydroxy-undecyl-oxy) -phenyl -] - 4,6-diphenyl-1,3,5-triazine of the mp 131-132 ° C.
Analysis C₃₂H₃₇N₃O₃ (511.67):
calculated: C 76.12; H 7,29; N 8,21;
Found: C, 75.06; H 7,46; N 8,13.

example 3 2- [2-hydroxy-4- (11-acryloyl-oxy-undecyl-oxy) -phenyl -] - 4,6-diphenyl-1, 3,5- triazine

A mixture of 51.2 g (0.1 mol) of 2- [2-hydroxy-4- (11-hydroxyundecyloxy) - phenyl] -4,6-diphenyl) -1,3,5-triazine, 22.2 g (0.22 mol) of triethylamine, 500 ml of toluene (Merck, 99.5%) under nitrogen is added dropwise within 20 min. at 15 to 20 ° C 13.3 g (0.105 mol) of 3-chloropropionic chloride added. The white suspension will filtered, the filtrate washed with water, dried with Na₂SO₄ and evaporated. The The residue is taken up in toluene, filtered through a bed of silica gel 60 and eluted with toluene. This gives 44.8 g (79.2%) of 2- [2-hydroxy-4- (11-acryloyloxy-undecyloxy) - phenyl] -4,6-diphenyl-1,3,5-triazine (Compound 102)  

as a white solid of mp. 123-125 ° C.
Analysis C₃₅H₃₉N₃O₄ (5,65,71):
calculated: C 74.31; H 6.95; N, 7.43%;
found: C 74.22; H 7.08; N 7.45%.

example 4 2- [2-hydroxy-4- (11-methacryloyloxy-undecyloxy) phenyl] -4,6-diphenyl-1, 3,5- triazine

The title compound (Compound 103) is prepared according to Example 3 Method produced; Melting point 94-96 ° C.

Example 4b Mixture of 2- [2-hydroxy-4- (3-vinylbenzyl-oxy) -phenyl -] - 4,6-bis- (2,4- dimethylphenyl) -1,3,5-triazine and 2- [2-hydroxy-4- (4-vinylbenzyl-oxy) -phenyl] -4,6-bis (2,4- dimethylphenyl) -1,3,5-triazine

The title compound (Compound 105) is given after that given in Example 8b Method produced; Mp .: 158-160 ° C

example 4c 2- [2-hydroxy-4- (2-methacryloyloxy-ethoxy) phenyl] -4,6-diphenyl-1,3,5 - triazin

The title compound (Compound 106) is obtained as a white solid by the method given in Example 3.
Analysis C₂₇H₂₃N₃O₄ (453.50):
calculated: C 71.57; H 5,11; N 9,27;
found: C 70.70; H 5.38; N 9.00.

example 5 2,4-bis (2,4-dimethylphenyl) -6- [2-hydroxy-4- (3-n-butyloxy-2-methacry-loyloxy propoxy -) - phenyl -] - 1,3,5-triazine

The title compound (compound 400) of melting point 3 ° C. is obtained according to the procedure described in Example 2 received specified method.

Intermediate for Example 6 2- [2-hydroxy-4- (11-hydroxy-undecyloxy) -phenyl -] - 4,6- bis- (2,4-dimethylphenyl) -1,3,5-triazine

Under nitrogen, a mixture of 79.5 g (0.2 mol) of 2- (2,4-dihydroxyphenyl) -4,6- (2,4-dimethylphenyl) -1,3,5-triazine, 11.2 g (0.2 mol) of powdered KOH (Fluka, <85%) in 500 ml diglyme (Fluka, 99%) heated to 80 ° C. Become the yellow solution 59.6 g (0.23 mol) of 11-bromo-1-undecanol (Fluka, 97%). The mixture will held at 100 ° C for 46 hours. It is then filtered hot and the filtrate Cooled to 0 ° C. The crystalline product is filtered, washed with hexane and at Dried 50 ° C / 70 mmHg.

This gives 81.0 g (71.4%) of 2- [2-hydroxy-4- (11-hydroxyundecyloxy) phenyl] -4,6-bis (2,4-dimethylphenyl) -1,3 , 5-triazines, as a pale yellow solid; F. 95-96 ° C.
Analysis C₃₆H₄₅N₃O₃ (567.78):
calculated: C 76.16; H 7.99; N, 7.40;
found: C, 75.42; H 7,92; N 7,39.

example 6 2- [2-hydroxy-4- (11-acryloyloxy-undecyloxy) phenyl] -4,6-bis (2,4- dimethylphenyl) -1,3,5-triazine (Compound No. 401)

Under nitrogen, a mixture of 56.8 g (0.1 mol) of 2- [2-hydroxy-4- (11-hydroxy undecyloxy) phenyl] -4,6-bis (2,4-dimethylphenyl) -1, 3,5-triazine, 12.4 g (0.1 33 mol) acryloyl chloride (Fluka, 97%), 0.4 g hydroquinone (Fluka, 98%) and 2.0 in pyridine in 500 ml toluene (Merck, 99 , 5%) for 30 hours at 80 ° C heated. The solution is then cooled to 50 ° C and treated with 21.3 ml (0.154 mol) of triethylamine, followed by another 6 hours at 70 ° C. Solid and solvent are separated and the solid yellow product is filtered through a layer of silica gel 60 with toluene. The product is recrystallized from isopropanol. This gives 47.0 g (75.5%) of 2- [2-hydroxy-4- (11-acryloyloxy undecyloxy) phenyl] -2,4-bis (2,4-dimethylph-enyl) -1,3 , 5-triazine of mp. 81-83 ° C.
Analysis C₃₉H₄₇N₃O₄ (621.82):
Calculated: C 75.33; H, 7.62; N 6.76;
Found: C 74.18; H 7.75; N 6,54.

example 7 2,4-bis (2,4-dimethylphenyl) -6- [2-hydroxy-4- (11-methacryloyloxy-unde cyloxy-) - phenyl -] - 1,3,5-triazine

The title compound (Compound 402) of melting point 71-73 ° C is after the in Example 6 obtained.

example 8a 2,4-bis (2,4-dimethylphenyl) -6- [2-hydroxy-4- (2-methacryloyloxy-ethox-y) - phenyl] -1,3,5-triazine

The title compound (compound 404) of melting point 132-133 ° C is after the in Example 3 obtained.

example 8b A mixture of 2- [2-hydroxy-4- (3-vinylbenzyl-oxy) -phenyl] -4,6-bis (2,4-bis) dimethylphenyl) -1,3,5-triazine and 2- [2-hydroxy-4- (4-vinylbenzyl-oxy) -phenyl] -4,6-bis (2,4- dimethylphenyl) -1,3,5-triazine (Compound No. 405)

Under nitrogen, a mixture of 19.9 g (0.05 mol) of 2- [2,4-dihydroxyphenyl] -4,6-bis (2,4-dimethylphenyl) -1,3,5-triazine, 8.4 g (0.055 mol) of vinylbenzyl chloride (Fluka, 98%, isomeric mixture of 70% meta and 30% para-vinylbenzyl chloride), 3.1 g (0.055 mol) of KOH and 100 in diglyme heated to 110 ° C for 3 hours , The suspension is cooled, 1 liter of water is added and the solid is filtered off and recrystallized from isopropanol. This gives 19.6 g (76.3%) of 2- [2-hydroxy-4- (3- / or4-vinylbenzyl-oxy) -phenyl -] - 2,4-bis (2,4-dimethylphenyl) - 1,3,5-triazine (Compound No. 405), m.p. 110-114 ° C.
Analysis C₃₄H₃₁N₃O₂ (513.64):
Calculated: C 79.51; H 6.08; N 8,18;
Found: C 79.53; H 5.98; N 7.98.

example 9

Under nitrogen, a mixture of 5.0 g (11 mmol) 2-phenyl-4,6-bis [2-hydroxy-4- (2-hydroxyethoxy) phenyl] 1,3,5-triazine, 3.4 g (33 mmol) Methacryloyl chloride 1.1 g (14 mmol) of pyridine in 35 ml of toluene at 80 ° C for 16 Heated for hours. The excess methacryloyl chloride and toluene are added 60 ° C / 60 mmHg away. After addition of 40 ml of toluene and 3.8 g (38 mmol) Triethylamine is heated at 80 ° C for 4 hours. It is allowed to cool and filtered solid residue. By column chromatography (Kieselgel 60; 230-400 mesh; Diameter 8 cm; h = 30 cm; Eluent toluene / ethyl acetate 1/1) gives 3.84 g of the Crude product, which is recrystallized from 180 ml of ethyl acetate. This gives 1.64 g 2-phenyl-4,6-bis [2-hydroxy-4- (2-methacryloyloxy-ethoxy) phenyl] 1,3, 5-triazine (Compound 201) as a yellowish solid (melting point: 154-159 ° C).

The ¹H-NMR spectrum (CDCl₃, 300 MHz) is in agreement with the desired product.
Elemental analysis for C₃₃H₃₁N₃O₈ (597.62):
Theory: C 66.32; H 5,23; N 7.03%;
Found: C, 66.04; H 5.37; N 7.03%.

example 10

Under nitrogen, a mixture of 12.7 g (20 mmol) 2-phenyl-4,6-bis [2-hydroxy-4- (3-n-butoxy-2-hydroxy-propoxy) phenyl -] 1,3,5-triazine, 4.3 g (46 mmol) of acryloyl chloride, 0.4 g (5 mmol) of pyridine in 80 ml of toluene at 70 ° C heated for 16 hours. After cooling to 50 ° C. and addition of 8.0 g (80 mmol) Triethylamine is heated at 80 ° C for 6 hours. It is allowed to cool and filtered solid residue ((CH₃CH₂) ₃N · HCl). The filtrate is evaporated and then in 200 ml of methylene chloride added. The solution is filtered through a Silica gel layer (Kieselgel 60, 230-400 mesh), washed with 450 ml of methylene chloride. To Removal of the solvent and drying at 80 ° C to obtain 8.8 g (59% yield) 2-Phenyl4,6-bis- [2-hydroxy-4- (3-n-butoxy-2-acryloyloxy-propoxy) phen-yl] 1,3,5-triazine (Compound 202) as an orange resin.

The ¹H-NMR spectrum (CDCl₃, 300 MHz) is in agreement with the desired product.
Elemental analysis for C₄₁ H₄₇N₃O₁₀ (741.84):
Theory: C 66.38; H 6,39; 5.66%;
Found: C 66.09; H 6,50; N 5.40%.

Preparation of the starting compound for Examples 11 and 12

Under nitrogen is added to a solution of 20.0 g (54 mmol) 2-phenyl-4,6-bis (2,4-dihydroxyphenyl) -1,3,5-triazine, 6.6 g (109 mmol) potassium hydroxide and 150 ml of diglyme at 80 ° C 32.4 g (128 mmol) of 11-bromo-1-undecanol. The Mixture is heated at 100 ° C for 14 hours. It is filtered off hot and the filtrate on Cooled to 0 ° C. The resulting crystallized solid is filtered off, pressed and 24 hours under reduced pressure (60 mmHg, 60 ° C.), followed by 27.6 g (72%). Yields 2-phenyl-4,6-bis [2-hydroxy-4- (11-hydroxy-undecyloxy-phenyl) -1,3,5-triazine as a pale yellow solid with the melting point 126-135 ° C receives.

The 1 H NMR spectrum (CDCl₃, 300 MHz) is consistent with the desired Product.

example 11

Under nitrogen, a mixture of 10.8 g (15 mmol) of 2-phenyl-4,6-bis- [2-hydroxy-4- (11-hydroxy-undecyloxy-phenyl) -1,3,5-triazine, 3.6 g (40 mmol) Acryloyl chloride, 0.2 g of hydroquinone, 0.3 g (3.8 mmol) of pyridine in 80 ml of toluene at 78 ° C heated for 16 hours. The excess acryloyl chloride and toluene are on Rotavapor removed. The residue is dissolved in 100 ml of toluene and after addition of 16.2 g (160 mmol) of triethylamine is heated at 80 ° C for 5 hours. Allow to cool and the solid residue ((CH₃CH₂) ₃N · HCl) is filtered off. The filtrate is evaporated and then taken up in 50 ml of methylene chloride. The solution is filtered through Silica gel (silica gel 60, 230-400 mesh, diameter 6 cm, h = 4 cm), washed with 400 ml Methylene chloride after and after removal of the solvent and two hours Dry (80 ° C / 0.1 mmHg) 10.7 g (86% yield) 2-phenyl-4,6-bis- [2-hydroxy-4- (11-acryloyloxy-undecyloxy-phenyl) -1,3,5-triazine (Compound 203) as pale yellow solid (mp: 93.3 ° C, determined by DSC).

The 1 H NMR spectrum (CDCl₃, 300 MHz) is consistent with the desired Product.  

example 12

Under nitrogen, a mixture of 10.8 g (15 mmol) of 2-phenyl-4,6-bis- [2-hydroxy-4- (11-hydroxy-undecyloxy-phenyl) -1,3,5-triazine, 4.0 g (38 mmol) Methacryloyl chloride, 0.2 g of hydroquinone, 0.3 g (3.8 mmol) of pyridine in 80 ml of toluene at Heated to 80 ° C for 16 hours. The excess methacryloyl chloride and toluene become removed at the Rotavapor. The residue is dissolved in 100 ml of toluene and after addition of 8.1 g (80 mmol) of triethylamine and 0.1 g of hydroquinone are heated at 70 ° C for 4 hours. It is allowed to cool and the solid residue ((CH₃CH₂) ₃N · HCl) is filtered off. The filtrate is evaporated and then taken up in 50 ml of methylene chloride. Filter the Solution through silica gel (silica gel 60, 230-400 mesh, diameter 6 cm, h = 4 cm), Washed with 400 ml of methylene chloride and after deduction of the solvent and drying for 2 hours (80 ° C / 0.1 mmHg) 10.9 g (85% yield) 2-phenyl-4,6-bis- [2-hydroxy-4- (11-acryloyloxy-undecyloxy-phenyl) -1,3,5-triazine (compound 204) as a light yellow solid (mp: 68.3 ° C, determined by DSC).

The 1 H NMR spectrum (CDCl₃, 300 MHz) is consistent with the desired Product.  

example 13

Compound (205) is obtained by the method described in Example 11. Tg = 17 ° C.
Analysis C₄₁H₄₇N₃O₈ (709.84):
Calculated: C 69.37; H, 6.67; N 5.92%;
Found: C 68.53; H, 6.67; N 6.03%.

example 14

Compound (206) is obtained by the method described in Example 11. Tg = 15 ° C.
Analysis C₃₉H₄₃N₃O₈ (681.79):
Calculated: C 68.71; H 6,36; N 6.16%;
Found: C 68.65; H, 6.44; N 6.49%.

Intermediate for Example 15 2-phenyl-4- (2-hydroxy-4-n-hexyloxy-phenyl) -6- [2- hydroxy-4- (11-hydroxy-undecyloxy) phenyl] -1,3,5-triazine

Under nitrogen, a mixture of 37.3 g of 2-phenyl-4,6-bis (2,4-dihydroxy phenyl) -1,3,5-triazines (0.100 mol), 6.6 g of powdered KOH (Fluka, <85%, 0.100 mol), 25.9 g of 11-bromo-1-undecanol (Fluka, 97%, 0.103 mol), and 0.6 g (3.6 mmol) Potassium iodide (Merck, 99.5%) in 160 ml diethylene glycol dimethyl ether (diglyin, Fluka, 99%) with stirring for 4.5 hours at 110 ° C heated. After cooling to 50 ° C, another 6.6 g (0.100 mol) of powdered KOH (Fluka, <85%) and 17.0 g (0.103 mol) of 1-bromohexane (Fluka, 98%). The mixture is stirred held at 105 ° C for 14 hours; then filtered hot and the filtrate evaporated at the Rotovapor. Column chromatography [Kieselgel 60, 230-400 mesh; 10 cm diameter; h = 30 cm; Eluiermittel CH₂Cl₂] provides the first eluted product the dihexyl derivative, the second eluted product is the desired title product; last, one obtains a proportion of one with 2 groups of 11-hydroxy-undecyl dialkylated compound.

After drying at 60 ° C / 60 mmHg for 24 h to obtain 22.5 g (35.8%) of 2-phenyl-4- (2-hydroxy-4-n-hexyloxy-phenyl) -6- [2-hydroxy 4- (11-hydroxy-undecylox-y) -phenyl] -1,3,5-triazine of mp. 96-99 ° C.
1 H NMR (CDCl₃, 300 MHz) spectrum is consistent with the desired product.
Analysis C₃₈H₄₉N₃O₅ (627.83):
Calculated: C 72.70; H 7,87; N 6.69%;
Found: C 72.19; H 8.01; N 6.88%

example 15 2-phenyl-4- (2-hydroxy-4-n-hexyloxy-phenyl) -6- [2-hydroxy-4- (11- methacryloyloxy undecyloxy) phenyl] -1,3,5-triazine (Compound 207)

Under nitrogen, a mixture of 22.0 g (35.0 mmol) of 2-phenyl-4- (2-hydroxy-4-n-hexyloxyphenyl) -6- [2-hydroxy-4- (11-hydroxy) undecyloxy) phenyl] -1,3,5-triazine, 4.4 g (42.0 mmol) methacryloyl chloride (Fluka, 97%) and 0.5 g (6.3 mmol) pyridine in 100 ml toluene (Merck, 99.5%) for 21 hours at 80-85 ° C heated. After cooling to 55 ° C., 8.9 g (87.5 mmol) of triethylamine (Fluka, 99.5%) are added. The mixture is held at 80 ° C for an additional 7 hours. It is then filtered hot and the filtrate is evaporated. The crude product (25.7 g) is dissolved in 120 ml CH₂Cl₂, filtered through a layer of silica gel 60 (230-400 mesh, 6.5 cm diameter, h = 5 cm) and eluted with 380 ml CH₂Cl₂. Separate the solvent and dry at 80 ° C / 0.1 mmHg for 2.5 h to provide 22.3 g (91.4%) of 2-phenyl-4- (2-hydroxy-4-hexyloxyphenyl) -6- [2 -hydroxy-4- (11-methacryloyloxy-undecyl-oxy) -phenyl] -1,3,5-triazine as an orange-colored resin; Tg = -13 ° C (DSC).
1 H NMR (CDCl₃, 300 MHz) spectrum is consistent with the desired product.
Analysis C₄₂H₅₃N₃O₆ (695.90):
Calculated: C, 72.49; H, 7.68; N 6.04%;
Found: C 72.14; H 7,48; N 5.98%.

example 16 2-phenyl-4- [2-hydroxy-4- (11-acetyloxy-undecyloxy) phenyl] -6- [2-hydroxy-4- (11- methacryloyloxy undecyloxy) phenyl] -1,3,5-triazine (Compound 208)

A mixture of 20.0 g (28.0 mmol) 2-phenyl-4,6-bis- [2-hydroxy-4- (11-hydroxy undecyloxy) phenyl] -1,3,5-triazine (intermediate for Examples 11 and 12), 3.1 g (29.4 mmol) Methacryloyl chloride (Fluka, 97%), 0.2 g of hydroquinone (Fluka, 98%), 0.3 g (3.8 mmol) Pyridine in toluene first heated for 5 hours at 80 ° C with stirring, then is cooled to 60 ° C, 4.62 g (58.8 mmol) of acetic acid chloride was added and the kept at 60 ° C with stirring for a further 18h. After separating the Solvent and the excess of acetic acid chloride (Rotavap) is dissolved in 100 ml  Dissolved toluene and after addition of 7.1 g (70 mmol) of triethylamine for 6 h with stirring Heated to 70 ° C. After cooling, the solid ([H₅C₂] ₃N · HCl) is filtered off and the filtrate evaporated. The crude product is dissolved in 100 ml of CH₂Cl₂, through a layer of Kieselgel 60 (230-400 mesh) and filtered with 1000 ml CH₂Cl₂ / methanol (95: 5) eluted. Separate the solvent and dry at 40 ° C / 60 mmHg for 48 h provide 20.8 g (90.1%) of the compound (208) of mp. 70-76 ° C.  

example 17

Under nitrogen, a mixture of 7.0 g (14.1 mmol) 2- (4-chlorophenyl) -4,6-bis [2-hydroxy-4- (2-hydroxy-ethoxy) -phenyl] -1,3,5-triazine, 8.52 g (94.1 mmol) acryloyl chloride, 0.3 g (3.8 mmol) of pyridine in 180 ml of toluene at 75 ° C heated for 14 hours. The excess acryloyl chloride and toluene are on Rotavapor removed. After addition of 100 ml of toluene and 5.0 g (48 mmol) of triethylamine is heated at 90 ° C for 14 hours. It is allowed to cool and the solid residue is filtered ((CH₃CH₂) ₃N · HCl). The filtrate is evaporated and recrystallized from ethyl acetate. This gives 4.4 g (52% yield) of 2- (4-chlorophenyl) -4,6-bis- [2-hydroxy-4- (2- acryloyloxyethoxy) phenyl] 1,3,5-triazine (Compound 200) as a yellowish solid (Melting point: 115-120 ° C).

The ¹H-NMR spectrum (CDCl₃, 300 MHz) is in agreement with the desired product.
Elemental analysis for C₃₁H₂₆ClN₃O₈ (604.02):
Theory: C, 61.64; H 4,34; N 6,96; Cl 5.87%;
Found: C 61.36; H 4:49; N 6,98; Cl 6.02%.

Intermediate for Examples 18 to 22b (i) 2-mesityl-4,6-dichloro-1,3,5-triazine

A solution of 109.5 g (0.55 mol) of 2-bromo-mesitylene (purity 98%) in 150 ml abs. THF (purity 99.5%) becomes one within 1½ hours under nitrogen stirred, tempered to 60 ° C suspension of 14.6 g (0.60 mol) of magnesium turnings (Purity 99.8%) in 100 ml abs. THF, to which an iodine crystal is added. The mixture is then held at reflux temperature for 30 minutes (68 ° C).

After cooling, the resulting Grignard reagent is transferred to a dropping funnel and dropwise to a solution of 96.0 g (0.52 mol) of cyanuric chloride (98%) in 270 ml of THF given. During the addition, which lasts 1 ½ hours, cooling is done by cooling Temperature maintained between 15 and 30 ° C. Then the mixture is at 25 ° C stirred for 2 hours, then to 2 liters of an ice-water mixture containing 80 ml 32% HCl (0.81 mol). After stirring for one hour, it is filtered. The filter cake is suspended in 1000 ml of water, stirred for 30 min and filtered again. This operation will repeated twice more. The filter cake is kept for 24 h at 25 ° C and a pressure of 60 mmHg (8000 Pa) dried over P₂O₅. 171.0 g of crude product are then in Dissolved toluene, filtered hot, and crystallized by the addition of hexane and cooling to 0 ° C. After filtration and drying 82.8 g of the title product (compound 18i)  receive

with the m.p. 85-91 ° C.
1 H-NMR (CDCl₃, 300 MHz): δ 2.22 (s, 6H); 2.32 (s, 3H); 6.95 (s, 2H).

(ii) 2-mesityl-4,6-bis (2,4-dihydroxyphenyl) -1,3,5-triazine

To a suspension of 130.0 g (0.485 mol) of 2-mesityl-4,6-dichloro-1,3,5-triazine (Compound 1) in 300 ml of gasoline boiling range 110-140 ° C and 385 ml sulfolane 148.7 g (1.21 mol) of anhydrous aluminum trichloride (purity 98%). The mixture heats up to 45 ° C. This is during 45 min. a solution of 133.5 g (1.21 mol) of resorcinol (purity 98%) in 155 ml of sulfolane. The mixture is heated to 80-85 ° C with evolution of HCl for 5 h 30 min. The upper phase (gasoline) is removed, the lower, viscous phase becomes hot in one stirred mixture of 2.1 l of methanol and 2.1 l of water. After stirring for the Duration of 14 h, the solid is filtered off, stirred in 2.2 l of 1-molar HCl for 1 h and filtered off again. The filter cake is suspended in 1000 ml of water, stirred for 30 min and filtered again. This operation is repeated twice more. The filter cake is dried for 24 h at 80 ° C and a pressure of 60 mmHg (8000 Pa). It will 170.5 g of the title product (compound 18ii) are of the formula

with the mp. 230-234 ° C.  

example 18

Compound (500) is obtained as a yellow resin by the method described in Example 10; D .: 9 ° C.
Analysis (C₄₄H₅₃N₃O₁₀) (783.92):
Calculated: C 67.42; H, 6.81; N 5.36%;
Found: C 67.27; H, 6.91; N 5.66%.

example 19

Compound (501) is obtained by the method described in Example 10 as a yellow resin; Tg .: -2 ° C.
Analysis (C₄₆H₅₇N₃O₁₀) (811.98):
Calculated: C 68.04; H 7.08; N 5.18%;
Found: C 68.01; H 7,10; N 4.92%.

example 20

Compound (502) is obtained by the method described in Example 12.
Analysis (C₅₄H₇₃N₃O₈) (892,19):
Calculated: C 72.70; H 8,25; N 4.71%;
Found: C 71.69; H 8.09; N 4.75%.

example 21

Compound (503) is obtained by the method described in Examples 9 and 11 as a yellow resin; D .: 22 ° C.
Analysis (C₄₄H₅₃N₃O₈) (751.92):
Calculated: C 70.28; H 7.11; N 5.59%;
Found: C 69.81; H 6,87; N 5.67%.

Intermediate for Examples 22 and 22b 2-mesityl-4- (2-hydroxy-4-n-hexyloxy-phenyl) -6- [2-hydroxy-4- (11-hydroxy-undecyloxy) phenyl] -1,3,5-triazine

Under nitrogen, a mixture of 83.0 g (0.200 mol) of 2-mesityl-4,6-bis- (2,4- dihydroxyphenyl) -1,3,5-triazine, 13.2 g (0.200 mol) of powdered KOH (Fluka, <85%), 51.8 g (0.206 mol) of 11-bromo-1-undecanol (Fluka, 97%) and 1.2 g (7.2 mmol) Potassium iodide (Merck, 99.5%) in 300 ml diethylene glycol dimethyl ether (diglyme, Fluka, 99%) with stirring for 3 hours at 120 ° C heated. After cooling to 60 ° C. Another 13.2 g of powdered KOH and 34.0 g of 1-bromohexane (0.206 mol; Fluka, 98%) was added. The mixture is stirred for 16 hours at 110 ° C.

It is then filtered hot and the filtrate is evaporated on a rotovapor. The crude product (152.1 g) is chromatographed [Kieselgel 60; 230-400 mesh; Column 10 cm diameter, h = 30 cm; Eluent: toluene / methanol 98: 2], the second fraction containing the desired product. After separating the solvent and drying at 110 ° C / 0.1 mmHg for 2 hours to obtain 55.2 g (41.2%) of 2-mesitylyl-4- (2-hydroxy-4-n-hexyloxy-phenyl) - 6- [2-hydroxy-4- (11-hydroxy-undecyloxy) -phenyl] -1,3,5-triazine as a yellow resin which slowly crystallizes at 25 ° C.
1 H NMR (CDCl₃, 300 MHz) spectrum is consistent with the title product.
Analysis (C₄₁H₅₅N₃O₅) (669.91):
Calculated: C 73.51; H 8,27; N 6.27%;
Found: C 73.55; H 8,47; N 6.29%.

example 22 2-mesityl-4- (2-hydroxy-4-n-hexyloxyphenyl) -6- [2-hydroxy-4- (11-methac-ryloyl oxy-undecyloxy) -phenyl] -1,3,5-triazine (Compound 504)

Under nitrogen, a mixture of 10.9 g (16.0 mmol) of 2-mesityl-4- (2-hydroxy-4-n- hexyloxyphenyl) -6- [2-hydroxy-4- (11-hydroxy-undecyloxy) -phenyl] -1,3,5-triazine, 2.0 g (19.2 mmol) of methacryloyl chloride (Fluka, 97%) and 0.4 g (5.0 mmol) of pyridine in 70 ml Toluene (Merck, 99.5%) for 16 hours at 80-85 ° C heated. After cooling to At 55 ° C, 4.1 g (40.0 mmol) of triethylamine (Fluka, 99.5%) are added.

It is then heated for a further 6 hours at 80 ° C and then filtered hot and the filtrate was evaporated. The crude product (13.6 g) is dissolved in 100 ml CH₂Cl₂, filtered through a silica gel 60 layer (230-400 mesh, 6.5 cm diameter, h = 4 cm) and eluted with 380 ml CH₂Cl₂. Remove the solvent and dry at 80 ° C / 0.1 mmHg for 2 hours 30 min. provides 22.3 g (91.4%) of 2-mesityl-4- (2-hydroxy-4-hexyloxyphenyl) -6- [2-hydroxy-4- (11-methacryloyloxy-undecyl-oxy) -phenyl] -1 3,5-triazine (compound 504) as a yellow resin; T: -10 ° C (DSC).
1 H NMR (CDCl₃, 300 MHz) spectrum is consistent with the title product.
Analysis (C₄₅H₅₉N₃O₆) (737.98):
Calculated: C 73.24; H 8.06; N 5.69%;
Found: C, 73.01; H 7,76; N 5.61%.

example 22a

Compound (505) is obtained by the method described in Example 8b as an orange resin; Tg. 13.3 ° C (DSC).
Analysis (C₄₂H₃₇N₃O₄) (647.78):
Calculated: C 77.88; H 5.76; N, 6.49%;
Found: C, 77.64; H 5.76; N 5.66%.

example 22b 2-mesityl-4- (2-hydroxy-4-n-hexyloxyphenyl) -6- [2-hydroxy-4- (11-acrylo-yloxy undecyloxy) -phenyl] -1,3,5-triazine (Compound 506)

Under nitrogen, a mixture of 27.3 g (40.8 mmol) of 2-mesityl-4- (2-hydroxy-4-n-hexyloxyphenyl) -6- [2-hydroxy-4- (11-hydroxyundecyloxy) -phenyl] -1,3-, 5-triazine, 4.4 g (49.0 mmol) acryloyl chloride (Fluka, 97%), 0.1 g (0.9 mmol) hydroquinone (Fluka, 99%) and 0 , 75 g (9.5 mmol) of pyridine in 170 ml of toluene (Merck, 99.5%) with stirring for 17 hours at 70-75 ° C heated. After cooling to 50 ° C., 20.0 g (197.6 mmol) of triethylamine (Fluka, 99.5%) are added. It is then heated for a further 6 hours at 85 ° C and then filtered hot and the filtrate was evaporated. The crude product is dissolved in 100 ml of a mixture of 98 parts by volume of toluene and 2 parts by volume of methanol, filtered through a silica gel 60 layer (230-400 mesh, 6.5 cm diameter, h = 5 cm) and treated with 400 ml of toluene. Methanol mixture eluted. Removal of the solvent and drying at 80 ° C / 0.1 mmHg for 3 hours yields 24.3 g (82.3%) of 2-mesityl-4- (2-hydroxy-4-hexyloxyphenyl) -6- [2-hydroxy -4- (11-acryloyloxy-undecyloxy) phenyl] -1,3,5-triazine (Compound 506) as a yellow resin; Tg. -14.2 ° C (DSC).
1 H-NMR (CDCl₃, 300 MHz) spectrum is consistent with the title product.
Analysis C₄₄H₅₇N₃O₆ (723.96):
Calculated: C 73.00; H 7,94; N 5.80%;
Found: C, 72.81; H 7.70; N 5.53%.

example 23

Under nitrogen, a mixture of 15.9 g (20 mmol) 2,4,6-Tris [2-hydroxy-4- (3-n-butoxy-2-hydroxypropoxy) phenyl] 1,3,5-triazine, 7.3 g (80 mmol) acryloyl chloride, 0.4 g (5 mmol) of pyridine in 120 ml of toluene at 75 ° C for 24 Heated with stirring for hours. The excess acryloyl chloride and toluene are on Rotavapor removed. The residue is dissolved in 100 ml of toluene and after addition of 10.1 g (100 mmol) of triethylamine is stirred for 6 hours at 80 ° C. Allow to cool and the solid residue ((CH₃CH₂) ₃N · HCl) is filtered off. The filtrate is evaporated and then taken up in 100 ml of methylene chloride. The solution is filtered through a Kieselgelschicht (silica gel 60, 230-400 mesh, diameter 10 cm, h = 5 cm), washed with 2000 ml of methylene chloride and after evaporation of the solvent and drying (90 ° C / 0.5 mmHg) 12.0 g (63% yield) 2,4,6-tris [2-hydroxy-4- (3-n-butoxy-2- acryloyloxy-propoxy) phenyl] 1,3,5-triazine (compound 300) as a light yellow resin.

The ¹H-NMR spectrum (CDCl₃, 300 MHz) is in agreement with the desired product.
Elemental analysis for C₅₁H₆₃N₃O₁₅ (958.07):
Theory: C, 63.94; H, 6.63; N 4.39%;
Found: C 63.24; H 6,57; N 4.02%.

Preparation of the starting compound for Examples 24 and 25

Under nitrogen is added to a solution of 20.3 g (50 mmol) 2,4,6-tris (2,4-dihydroxyphenyl) -1,3,5-triazine, 9.3 g (141 mmol) of potassium hydroxide and 150 ml of diglyme at 80 ° C 42.9 g (170 mmol) of 11-bromo-1-undecanol given. The Mixture is heated at 100 ° C for 16 hours. It is filtered off hot and the filtrate on Cooled to 0 ° C. The crystallized solid is filtered off, pressed and 48 hours under reduced pressure (60 mmHg; 70 ° C), followed by 24.3 g (53% yield). 2,4,6-tris [2-hydroxy-4- (11-hydroxy-undecyloxy) -phenyl] -1,3,5-triazi-n as pale yellow, resin-like solid receives.

The 1 H NMR spectrum (CDCl₃, 300 MHz) is consistent with the desired Product.

example 24

Under nitrogen, a mixture of 10.1 g (11 mmol) 2,4,6-tris  [2-hydroxy-4- (11-hydroxy-undecyloxy-phenyl) -1,3,5-triazine, 3.6 g (40 mmol) Acryloyl chloride, 0.2 g of hydroquinone, 0.3 g (3.8 mmol) of pyridine in 80 ml of toluene at 80 ° C heated for 18 hours. The excess acryloyl chloride and toluene are on Rotavapor removed. The residue is dissolved in 100 ml of toluene and after addition of 16.2 g (160 mmol) of triethylamine and 0.1 g of hydroquinone are kept at 78 ° C for 5 hours touched. It is allowed to cool and the solid residue ((CH₃CH₂) ₃N · HCl) is filtered off. The Filtrate is evaporated and then taken up in 100 ml of methylene chloride. you the solution is filtered through a layer of silica gel (Kieselgel 60, 230-400 mesh; Diameter 6 cm; h = 4 cm), washed with 400 ml of methylene chloride and after Removal of the solvent and drying for 2 hours (70 ° C / 0.1 mmHg) 7.7 g (65%) Yield) 2,4,6-Tris [2-hydroxy-4- (11-acryloyloxy undecyloxy) phenyl] -1,3,5-t-riazine (Compound 301) as a light yellow solid (mp: 72.8 ° C, determined by DSC).

The 1 H NMR spectrum (CDCl₃, 300 MHz) is consistent with the desired Product.

example 25

Under nitrogen, a mixture of 10.1 g (11 mmol) 2,4,6-tris [2-hydroxy-4- (11-hydroxy-undecyloxy-phenyl) -1,3,5-triazine, 4.2 g (40 mmol) Metacryloyl chloride, 0.2 g of hydroquinone, 0.3 g (3.8 mmol) of pyridine in 80 ml of toluene at Heated to 80 ° C for 18 hours. The excess acryloyl chloride and toluene are on Rotavapor removed. The residue is dissolved in 100 ml of toluene and after addition of 8.1 g (80 mmol) of triethylamine and 0.1 g of hydroquinone are stirred for 5 hours at 70 ° C. It is allowed to cool and the solid residue is filtered off. The filtrate is evaporated and then taken up in 100 ml of methylene chloride. The solution is filtered through a Silica gel layer (silica gel 60, 230-400 mesh, diameter 6 cm, h = 4 cm), washed with 400 ml of methylene chloride and after deduction of the solvent and drying for 2 hours (70 ° C / 0.1 mmHg) 7.7 g (65% yield) 2,4,6-tris [2-hydroxy-4- (11-methacryloyloxy-undecyloxy-phenyl) -1,3,5-triazine (Compound 302) as a light yellow solid (mp: 60.2 ° C, determined by DSC).

The 1 H NMR spectrum (CDCl₃, 300 MHz) is consistent with the desired Product.  

example 28

Homopolymer of 2-phenyl-4- (2-hydroxy-4-hexyloxyphenyl) -6- [2-hydroxy-4- (11-methacryloyl-oxy-undecyl-oxy) -phenyl] -1,3,5-triazine (Compound 602). In a 100 ml three-necked flask under argon, a solution of 5.2 g (7.5 mmol) 2- (phenyl) -4- (2-hydroxy-4-hexyloxyphenyl) -6- (2-hydroxy-11-methacrylo-yloxy undecyl-oxyphenyl) -1,3,5-triazine (Compound 207) in 40 ml toluene (Fluka, 99.5%) with 40 mg (0.22 mmol) of α, α'-azo-isobutyronitrile (AIBN, Fluka, 98%) and 70 mg (0.75 mmol) of n-butyl-mercaptan (Fluka, 97%).

The mixture is kept at 85 ° C with stirring for 16 hours. After cooling, it is the clear yellow solution dropwise with stirring to a solution of 400 ml Acetonitrile (Fluka, 99.5%).

The precipitate is decanted and taken up in 30 ml of toluene. After removal of the solvent and drying for two hours at 80 ° C / 0.1 mmHg to obtain 3.35 g (64%) of the title product (compound 602); D .: 29.9 ° C.
1 H NMR (CDCl₃, 300 MHz) Spectrum is consistent with the desired product. (no vinyl H signal)

MALDI-MS:
Mn = 1698
Mw = 3251

example 29 Copolymer of 2-phenyl-4- (2-hydroxy-4-hexyl-oxy-phenyl) -6- [2-hydroxy-4- (11- methacryloyloxy-undecyloxy) -phenyl] -1,3,5-triazine and n-butyl acrylate in the molar ratio 1: 4

In a 100 m three-necked flask under argon, a solution of 5.2 g (7.5 mmol) 2- (phenyl) -4- (2-hydroxy-4-hexyloxyphenyl) -6- (2-hydroxy-11-methacrylo-yloxy-undecyl oxyphenyl) -1,3,5-triazine (Compound 207) and 3.8 g (30 mmol) of n-butyl acrylate (Fluka, 99%) in 40 ml of toluene (Fluka, 99.5%) with 200 mg (1.12 mmol) of α, α'-azo isobutyronitrile (AIBN, Fluka, 98%) and 300 mg (3.75 mmol) of n-butyl-mercaptan (Fluka, 97%).

The mixture is kept at 85 ° C with stirring for 17 hours. After cooling, it is the clear yellow solution dropwise with stirring to a solution of 400 ml Acetonitrile (Fluka, 99.5%).  

The precipitate is decanted and taken up in 30 ml of toluene; firm Impurities are removed by filtration. After deduction of the solvent and dried for 2 hours at 80 ° C / 0.1 mmHg to obtain 6.60 g (73%) of Title product (Compound 603); T: -3.5 ° C.

MALDI-MS:
Mn = 2905
Mw = 4199

example 30

Compound (604) is prepared according to the method given in Example 28 manufactured; This gives an orange-yellow resin, Tg. = 49.8 ° C.

[C₄₅H₅₉N₃O₆] (737.98):
calculated: C 73.24; H 8.06; N 5.69%;
found: C, 72.57; H 8,43; N 5.49%;

MALDI-MS:
Mn = 1920
Mw = 4198

example 31

Compound (605) is prepared according to the method given in Example 29 manufactured; This gives an orange resin Tg. = -4,2 ° C.

[C₄₅H₅₉N₃O₆] ₁ [C₇H₁₂O₂] ₄:
calculated: C 70.11; H, 8.62; N 3.36%;
Found: C, 70.71; H, 8.74; 3.67% N;

MALDI-MS:
Mn = 3238
Mw = 4923

example 31a

Compound (606) is made according to the method given in Example 29 prepared using instead of n-butyl acrylate 30 mmol of n-dodecyl methacrylate become; Tg. -33.4 ° C.

MALDI-MS:
Mn = 2023 g / mol
Mw = 3661 g / mol

example 32

Compound (607) is prepared according to the method given in Example 28; This gives a white solid.
[C₃₅H₃₉N₃O₄] (565.71):
calculated: C 74.31; H 6.95: N 7.43%;
found: C 74.13; H, 7.16: N, 7.27%;

(MALDI-MS)
Mn = 1938
Mw = 3054

example 33

Compound (608) is prepared according to the method given in Example 29.
[C₃₅H₃₉N₃O₄] ₁ [C₇H₁₂O₂] ₄:
calculated: C 70.17; H 8,13; N 3.90;
found: C 70.70; H 8,33; N 4.60%;

MALDI-MS:
Mn = 2310
Mw = 3341

example 34

Compound (609) is prepared according to the method given in Example 28; You get a yellow resin.
[C₄₀H₄₉N₃O₄] (635,85):
calculated: C 75.56; H 7,77; N 6.61%;
Found: C, 74.02; H 8.06; N 6.06%;

Mn = 1781
Mw = 3669 (MALDI-MS)

example 35

Compound (610) is prepared by the method given in Example 29, but using only half the amount of n-butyl acrylate.
[C₄₀H₄₉N₃O₄] ₁ [C₇H₁₂O₂] ₂:
calculated: C 72.70; H 8,25; N 4.71%;
found: C, 71.81; H, 8.41; N 4.68%;

GPC: Mn = 1908
Mw = 3111

example 36

Compound (611) is prepared by the method given in Example 28; a yellow solid of melting point 85.7 ° C. (DSC) is obtained.
[C₃₆H₄₁N₃O₄] (579.74):
Calculated C 74.58 H 7,13 N, 7.25%;
found C 73.90 H 7,15 N 7,03%;

Mn = 2405
Mw = 3701 (MALDI-MS)

example 37

Compound (612) is prepared according to the method given in Example 35; This gives a yellow resin, Tg. = 15.8 ° C.
[C₃₆H₄₁N₃O₄] ₁ [C₇H₁₂O₂] ₂:
Calcd C 71.83 H 7.84 N 5.03%;
found C 71.71 H 7.61 N 5.19%;

Mn = 3241
Mw = 4920 (MALDI-MS)

example 38

Compound (613) is prepared by the method given in Example 28; a yellow solid is obtained, Tg. = 59.1 ° C.
[C₃₆H₄₁N₃O₅] (595.74):
calculates C 72.58; H 6,94; N 7.05%;
found C 72.25; H 6.95; N 6.63%;

Mn = 2405
Mw = 5533 (MALDI-MS)

example 39

Compound (614) is prepared according to the method given in Example 35; This gives an orange resin, Tg. = 35.7 ° C.
[C₃₆H₄₁N₃O₅] ₁ [C₇H₁₂O₂] ₂:
Calculates C 70.48; H, 7.69; N 4.93%;
found C 70.61; H 7,76; N 5.35%;

Mn = 3612
Mw = 5264 (MALDI-MS)

example 40

Compound (615) is prepared according to the method given in Example 35 manufactured; Tg. 66.5 ° C.

MALDI-MS:
Mn = 2111 g / mol
Mw = 3174 g / mol

example 41

Compound (616) is prepared according to the method given in Example 35; Tg. 59.8 ° C.
[C₃₄H₃₁N₃O₂] ₁ [C₇H₁₂O₂] ₂:

MALDI-MS:
Mn = 2223 g / mol
Mw = 3634 g / mol

example 42

Copolymer of methyl methacrylate and compound (103) Methyl methacrylate is used with 1% by weight of Compound No. 103 according to the following Method polymerized:

A mixture of 70.0 g of methyl methacrylate, 0.7 g of the compound (103) and 0.07 g of lauroyl peroxide is heated to 60 ° C. by heating in a water bath prepolymerized until syrupy but still pourable. The prepolymer is in the prepared casting mold (2 glass plates 160 × 210 × 6 mm, PVC insulated wire d = 1.5 mm, 6 metal clips), polymerized in a water bath for 6 h at 60 ° C and then cured in a convection oven for 3 h at 120 ° C. One receives plates of approx. 1.5 mm thickness.

0.3 g of the obtained modified polymethyl methacrylate (PMMA) are dissolved in CHCl₃ dissolved (solution I, 0.06 g PMMA / l) and the UV spectrum measured. Subsequently the polymer is precipitated by the addition of methanol, filtered off, dried and then again dissolved in CHCl₃ (solution II, 0.04 g PMMA / l). Also of solution II the UV spectrum is registered.

Based on the molecular weight of the monomer (103) and assuming constant concentration of the chromophore in the polymer is measured from the UV spectra for the wavelength 342 nm, respectively, the molar extinction coefficient determined:

Solution I: ε₃₄₂ = 20,700
Solution II: ε₃₄₂ = 22 200

The constant extinction coefficient before and after reprecipitation shows that the monomer (103) is incorporated in the polymer.

example 43

Copolymer of methyl methacrylate and compound (402) Methyl methacrylate is reacted with 1% by weight of Compound No. 402 according to Example 42 polymerized method. Samples of the resulting polymer are as in Example 42 described on incorporation of the monomer of the invention investigated. It the following data is determined:

Solution I: ε₃₃₉ = 21,600
Solution II: ε₃₃₉ = 22 200

The constant extinction coefficient before and after reprecipitation shows that the monomer (402) is incorporated in the polymer.  

B) Application Examples B1: Modified PMMA

5 g each modified polymethyl methacrylate from Examples 42 and 43 (containing 1% copolymerized stabilizer [103] and [402]) are in 30 g of methylene chloride at Room temperature dissolved. From this solution films are drawn on glass plates, the after evaporation of the solvent and drying in vacuo, a thickness of 30 microns to have. For comparison, a similar film of unstabilized Polymethyl methacrylate prepared (Plex® 8704, Röhm & Haas A.G.).

The films are peeled off the glass plates and placed in cardboard frames (6 × 3 cm) curious; excited. These samples are placed in a UV illuminator with 5 fluorescent lamps TL / 09 and 5 lamps TL / 12, which are mounted 20 cm above the samples, irradiated (waves length range 295-400 nm). Before irradiation and at regular intervals during The irradiation is the discoloration of the samples by measuring the yellowness index (YI, method ASTM D 1925). Table I summarizes the results.

Table 1

YI of PMMA containing 1% stabilizer in copolymerized form

The stabilizers according to the invention cause virtually no discoloration of the Substrate.

example 86

The UV absorbers according to the invention [compounds (202), (600) or (601)] are pre-dissolved in about 5-10 g of xylene and the following in a clearcoat Incorporated composition:

The thus prepared clearcoat is treated with butyl glycol acetate / n-butanol / xylene (1/6/13) Sprayability diluted and applied to a prepared substrate (coil coat Aluminum sheet, automobile filler, silver metallic basecoat) applied. After a Flash off time of about 15 minutes is baked at 130 ° C for 30 minutes. It results in one Dry film thickness of about 40-45 microns.

As a comparison serves a manufactured in the same way clearcoat of none Contains UV absorber.

The samples are weathered in a UVCON® device (Atlas Corp.). (UVB-313 lamps, cycle: 8 h UV, 70 ° C, 4 h cond., 50 ° C)
The 20 ° gloss (DIN 67 530) is measured. The stabilized samples show better gloss retention than the unstabilized control.

Claims (19)

1. Compound of formula I wherein the radicals
E₁ and E₂, independently of one another, each represent a group of the formula Ia or Ib and in which
A -C (= O) -CR₅ = CR-R₆; -CH₂-C (= CH₂) -R₁₀,
- (CH₂) _p -SiR₁₁R₁₁'-CH = CH₂, C (= O) - (CH₂) _q -CH = CH₂, or -C (= O) -O-CH₂-C (= CH₂) -R₁₀; and,
in the case that R₃ 'has the meaning -O-CR₈R₈' - (CH₂) ₁-XA, R₁ additionally has the meanings C₁-C₁₈-alkyl and C₃-C₂₀-alkyl, which is represented by -O-, -CO-O- or - O-CO- is interrupted, including; and in the case that E₁ is a group of the formula Ia, wherein none of the radicals R₂ and R₁₄
Hydrogen, R₁ is additionally the meanings -A, -CH₂-CH (XA) -CH₂-O-R₇, -CR₈R'₈- (CH₂) ₁-XA, -CH₂-CH (OA) -R₉, -CH₂-CH (OH) -CH₂-XA,
-CHR₈- (CH₂) _r -C (= O) -O-CH₂-CH (OH) -CH₂-OA and -CR₈R'₈- (CH₂) ₁-C (= O) -XA; and
in case E₁ is a group of formula Ib, R₁ additionally comprises -CH₂-CH (XA) -CH₂-O-R₇;
R₂, independently of one another, is H, C₁-C₁₂-alkyl, cyclohexyl, C₃-C₆-alkenyl, halogen, phenyl or trifluoromethyl;
R₂ ', independently, C₁-C₁₈ alkoxy, C₃-C₁₈ alkenoxy, -OH or -O-CO-R₁₂;
R₃ and R₃ 'are independently H, -OH, -O-CH₂-CH (XA) -CH₂-O-R₇, -O-CH₂-C (= CH₂) -R₁₀, -O- (CH₂) _p -SiR₁₁R₁₁'-CH = CH₂, -OC (= O) - (CH₂) _q -CH = CH₂, -OC (= O) -O-CH₂-C (= CH₂) -R₁₀, -O-CR₈R₈ '- (CH₂) ₁-XA, -O-CH₂-CH (OA) -R₉, -O-CH₂-CH (OH) -CH₂- XA, -O-CHR _8- (CH₂) _r -C (= O) -O-CH ₂ -CH (OH) -CH ₂ -OA,
-CR₈R'₈- (CH₂) ₁-C (= O) -XA, C₁-C₁₈-alkyl, C₆-C₁₂-cycloalkyl, C₃-C₁₈-alkenyl, -OR₁₃₁, halogen, trifluoromethyl, phenyl, phenyl-C₁-C₄ -alkyl, -CN, C₁-C₁₈-alkyl-S (= O) _t - or
Phenyl-S (= O) _t -;
R₄, R₄ 'and R₄'', independently of one another, H, C₁-C₁₈-alkyl, C₃-C₆-alkenyl, -OR₁₃₁, halogen, trifluoromethyl, phenyl, phenyl-C₁-C₄-alkyl, having one to three radicals C₁- C₄-alkyl-substituted phenyl-C₁-C₄-alkyl, -CN, C₁-C₁₈-alkyl-S (= O) _t - or phenyl-S (= O) _t -;
R₅ is H, -CH₂-COOR₁₃, C₁-C₄-alkyl or -CN;
R₆ is H, -COOR₁₃, C₁-C₁₇-alkyl or phenyl;
R₇ is C₁-C₁₈ alkyl; C₅-C₁₂ cycloalkyl; C₃-C₁₈ alkenyl; phenyl; with one to three radicals C₁-C₈-alkyl, C₁-C₈-alkoxy, C₃-C₈-alkenoxy, halogen or trifluoromethyl-substituted phenyl; Phenyl-C₁-C₄-alkyl; interrupted by one or more -O- interrupted C₃-C₅₀-alkyl; 1-adamantyl, 2-adamantyl, norbornyl, norbornane-2-methyl, or -C (= O) R₁₂;
R₈ and R₈ ', independently of one another, H or C₁-C₁₈-alkyl, phenyl, phenyl-C₁-C₈-alkyl, or having 1 to 3 radicals C₁-C₄-alkyl, C₃-C₈-alkenoxy, C₁-C₈-alkoxy, Halogen, CF₃ substituted phenyl;
R₉ is C₁-C₁₈ alkyl, phenyl or phenyl-C₁-C₄ alkyl;
R₁₀ is H or -CH₃,
R₁₁ and R₁₁ 'are independently C₁-C₄ alkyl or phenyl or phenyl substituted with one to three C₁-C₈ alkyl, C₁-C₈ alkoxy, C₃-C₈ alkenoxy, halogen or trifluoromethyl;
R₁₂ H, C₁-C₁₈ alkyl, C₂-C₁₈ alkenyl, phenyl, phenyl-C₁-C₄-alkyl, C₅-C₁₂-cycloalkyl, C₁-C₁₂ alkoxy, phenoxy, norbornan-2-yl, 5-norbornene-2 -yl, 1-adamantyl;
R₁₃ is H, C₁-C₁₈ alkyl, C₃-C₁₈ alkenyl, phenyl, C₅-C₁₂ cycloalkyl, C₃-C₅₀ alkyl interrupted by one or more -O-; with one to three radicals C₁-C₈-alkyl, C₁-C₈-alkoxy, C₃-C₈-alkenoxy, halogen or trifluoromethyl-substituted phenyl;
Phenyl-C₁-C₄-alkyl; 1-adamantyl; 2-adamantyl; Norbornyl, norbornane-2-methyl;
R₁₄ and R₁₅, independently of one another, H, C₁-C₁₈-alkyl, C₃-C₁₈-alkenyl, C₆-C₁₂-cycloalkyl, halogen, CF₃, phenyl, phenyl-C₁-C₄-alkyl, CN, C₁-C₁₈-alkyl-S (= O) _t - or phenyl-S (= O) _t - or -OR₁₃₁;
R₁₃₁ C₁-C₁₈ alkyl; C₃-C₁₈ alkenyl; C₁-C₁₈-alkyl which is substituted by OH, C₁-C₁₈-alkoxy, C₅-C₁₂-cycloalkoxy, C₃-C₆-alkenyloxy, halogen, -COOR₁₃, -CONH₂, -COHNR₁₃₂, -CON (R₁₃₂) (R₁₃₃), -NHCOR₁₂, CN, -OCOR₁₂, phenoxy, and / or by C₁-C₁₈-alkyl, C₁-C₁₈-alkoxy or halogen-substituted phenoxy; C₃-C₁₈ alkenyl;
C₆-C₁₂ cycloalkyl; C₆-C₁₂-cycloalkyl substituted by C₁-C₄alkyl and / or -OCOR₁₂; interrupted by one or more -O- interrupted C₃-C₅₀-alkyl which is unsubstituted or substituted by OH or O-CO-R₁₂; phenyl; Phenyl-C₁-C₄-alkyl;
-COR₁₂; -SO₂R₁₂;
R₁₃₂ and R₁₃₃, independently, C₁-C₁₂ alkyl, C₃-C₁₂ alkoxyalkyl, C₄-C₁₆ dialkylaminoalkyl, C₅-C₁₂ cycloalkyl; or
R₁₃₂ and R₁₃₃ together C₃-C₉-alkylene, C₃-C₉-oxaalkylene or -Azaalkylen;
X is -NR₈-, -O-, NH- (CH ₂ ) -NH- or O- (CH ₂ ) -NH-;
k is a number 2-4;
l is a number 0-19;
m is a number 2-8;
n is a number 0-4;
p is a number 0-10;
q is a number 1-8;
r is a number 0-18; and
t is a number 0, 1 or 2. 2. Compound of the formula Ic wherein the radicals
A is -C (= O) -CR₅ = CH-R₆;
R₁, independently of one another, -CH₂-C (= CH₂) -R₁₀, - (CH₂) _p -SiR₁₁R₁₁'-CH = CH₂, -C (= O) - (CH₂) _q -CH = CH₂, or -C (= O) -O- CH₂-C (= CH₂) -R₁₀; and
in case R₂ 'is OH or OA, R₁ additionally comprises -CH₂-CH (OA) -CH₂-O-R₇;
R₂ and R₂ 'are independently H, -OH, -OA, C₁-C₁₂ alkyl, cyclohexyl, C₃-C₆ alkenyl, C₁-C₁₈ alkoxy, C₂-C₁₈ alkenoxy, halogen, phenyl or trifluoromethyl;
R₃ and R₃ 'are independently H, -OH, -OA, the above-mentioned -OR₁, -O-CHR₈- (CH₂) ₁-OA, -O-CH₂-CH (OA) -R₉, -O-CH₂ -CH (OH) -CH₂-OA, -O-CHR _8- (CH₂) _r -C (= O) -O-CH ₂ -CH (OH) -CH ₂ -OA, C₁-C₁₂-alkyl, cyclohexyl, C₃-C₆-alkenyl, C₁-C₁₈-alkoxy, C₃-C₁₈-alkenoxy, halogen, trifluoromethyl, phenyl, phenyloxy, phenyl-C₁-C₄-alkyl, phenyl-C₁-C₄-alkoxy, -CN, C₁-C₁₈-alkyl -S (= O) _t - or phenyl-S (= O) _t -;
R₄, R₄ 'and R₄'', independently of one another, H, C₁-C₁₂-alkyl, C₃-C₆-alkenyl, C₁-C₁₈-alkoxy, C₃-C₁₈-alkenoxy, halogen, trifluoromethyl, phenyl, phenyloxy, phenyl-C₁- C₄-alkyl, substituted with one to three radicals C₁-C₄-alkyl-substituted phenyl-C₁-C₄-alkyl, phenyl-C₁-C₄-alkoxy, -CN, C₁-C₁₈-alkyl-S (= O) _t - or
Phenyl-S (= O) _t -;
R₅ is H, -CH₂-COOR₁₃, C₁-C₄-alkyl or -CN;
R₆ is H, -COOR₁₃, C₁-C₁₇-alkyl or phenyl;
R₇ is C₁-C₁₈-alkyl, cyclohexyl, C₃-C₁₈-alkenyl, phenyl, with one to three radicals C₁-C₈-alkyl, C₁-C₈-alkoxy, C₂-C₈-alkenoxy, halogen or trifluoromethyl-substituted phenyl, phenyl-C₁- C₄-alkyl, or -C (= O) -R₁₂;
R₈ is H or C₁-C₁₈ alkyl;
R₉ is C₁-C₁₈ alkyl, phenyl or phenyl-C₁-C₄ alkyl;
R₁₀ is H or -CH₃;
R₁₁ and R₁₁ 'are independently C₁-C₄ alkyl or phenyl or phenyl substituted with one to three C₁-C₈ alkyl, C₁-C₈ alkoxy, C₃-C₈ alkenoxy, halogen or trifluoromethyl;
R₁₂ is C₁-C₁₈ alkyl, C₂-C₁₈ alkenyl or phenyl;
R₁₃ is H, C₁-C₁₈ alkyl, C₃-C₁₈ alkenyl or phenyl;
l is a number 0-19;
p is a number 0-10;
q is a number 1-8;
r is a number 0-18; and
t is a number 0, 1 or 2. 3. A compound according to claim 1 of the formula (I), wherein the radicals
R₂ is H, C₁-C₄ alkyl, C₃ alkenyl, F, Cl or phenyl;
R₂'C₁-C₄alkoxy, C₃-alkenoxy, -O-CO-R₁₂ or -OH;
R₃ and R₃ 'are independently H, -OH, -O-CH₂-CH (XA) -CH₂-O-R₇, -O-CHR₈- (CH₂) ₁-XA, -O-CH₂-CH (OA) -R₉, -O-CH₂-CH (OH) -CH₂-XA, C₁-C₄-alkyl, cyclohexyl, C₃-alkenyl, -OR₁₃₁, F, Cl, trifluoromethyl, phenyl, benzyl or -CN;
R₄ 'and R₄'', independently of one another, H, C₁-C₄-alkyl, C₃-alkenyl, C₁-C₄-alkoxy, C₃-alkenoxy, F, Cl, trifluoromethyl, phenyl, phenyl-C₁-C₃-alkyl or -CN ;
R₅ is H or -CH₃;
R₆ is H, -COOR₁₃, -CH₃ or phenyl;
R₇ is C₁-C₈-alkyl, cyclohexyl, C₃-C₈-alkenyl, phenyl, phenyl or benzyl substituted with one to three radicals C₁-C₄-alkyl or C₁-C₄-alkoxy;
R₉ is C₁-C₁₀ alkyl, phenyl or benzyl;
R₁₁ and R₁₁ ', independently of one another, C₁-C₄-alkyl or phenyl;
R₁₂ is H, C₁-C₁₈-alkyl, C₂-C₃-alkenyl, phenyl, phenyl-C₁-C₄-alkyl or cyclohexyl;
R₁₃ is C₁-C₄alkyl, C₃-alkenyl, cyclohexyl, phenyl-C₁-C₄alkyl or phenyl;
R₄, R₁₄ and R₁₅, independently, H, C₁-C₈ alkyl, F, Cl, C₁-C₄ alkoxy, CF₃, phenyl, or CN;
R₁₃₁ C₁-C₁₈ alkyl; C₃-C₁₈alkyl which is substituted by OH, C₁-C₁₈alkoxy, C₅-C₁₂-cycloalkoxy, -COOR₁₃, -CONH₂, -COHNR₁₃₂, -CON (R₁₃₂) (R₁₃₃), -NHCOR₁₂, CN, -OCOR₁₂ and / or phenoxy; C₃ alkenyl; C₆-C₁₂ cycloalkyl; interrupted by one or more -O- interrupted C₃-C₅₀-alkyl which is unsubstituted or substituted by OH or OCOR₁₂; phenyl; Phenyl-C₁-C₄-alkyl; -COR₁₂; -SO₂R₁₂;
X is -O- or -NR₈-;
l is a number 1-19; and
r is a number 0-10. 4. A compound according to claim 1 of the formula (I), wherein E₁ and E₂, independently of one another, represent a group of the formula Ia or Ib and in which means, or in the case that R₃ '
-O-CR₈R₈ '- (CH₂) ₁-XA, R₁ additionally has the meanings C₁-C₁₂-alkyl and C₆-C₁₈-alkyl which is interrupted by -O-, -CO-O- or -O-CO-, includes; in case E₁ is a group of formula Ib, R₁ additionally comprises -CH₂-CH (OA) -CH₂-O-R₇; such as
in the case where E₁ is a group of the formula Ia in which none of the radicals R₂ and R₁₄ is hydrogen, R₁ additionally has the meanings -CH₂-CH (OA) -CH₂-O-R₇, -CR₈R'₈- (CH₂) ₁- XA, -CH₂-CH (OA) -R₉ and -CH₂-CH (OH) -CH₂-XA include; R₂ is H, CH₃ or Cl;
R₂'-OH;
R₃ is H, -CH₃, C₁-C₄-alkoxy, C₃-alkenoxy, F, Cl, phenyl, benzyloxy or -CN;
R₃ 'is -OH, -O-CH₂-CH (XA) -CH₂-O-R₇, -O-CH₂- (CH₂) ₁-XA, -O-CH₂-CH (OA) -R₉, -O-CH₂-CH (OH) -CH₂-XA, or -OR₁₃₁; R₄, R₁₄ and R₁₅ independently represent H, F, Cl, OCH₃ or CH₃;
the radicals R₄ 'and R₄''are meta to the triazine ring and, independently of one another, H, -CH₃, C₃-alkenyl, -OCH₃, C₃-alkenoxy, F, Cl, phenyl-C₃-alkyl or -CN;
R₅ is H or -CH₃;
R₆ H;
R₇ is C₁-C₈alkyl, cyclohexyl, C₃-alkenyl, phenyl or benzyl;
R₈ and R₈'H;
R₉ is C₁-C₁₀ alkyl;
R₁₂ is C₁-C₁₈ alkyl, phenyl or cyclohexyl;
R₁₃₁ C₃-C₁₈ alkyl or C₃-C₁₈ alkyl which is substituted by OH, C₁-C₁₈ alkoxy, -NHCOR₁₂ and / or -OCOR₁₂; and
l is a number 1-19. 5. Polymer compound obtainable by addition polymerization of at least one compound of formula (Id) or at least one compound of formula (Id) and at least one further ethylenically unsaturated compound wherein the radicals
E₁ and E₂, independently of one another in each case represent a basis of the formula If or Ig and in which
A is -C (= O) -CR₅ = CH-R₆;
R₁ independently of one another, -CH₂-CH (XA) -CH₂-O-R₇, -CR₈R₈ '- (CH₂) ₁-XA,
-CH₂-CH (OA) -R₉, -CH₂-C (= CH₂) -R₁₀, - (CH₂) _p -S-R₁₁R₁₁'-CH = CH₂, C (= O) - (CH₂) _q -CH = CH₂, -CHR₈- (CH₂) _r -C (= O) -O-CH₂-CH (OH) -CH₂-OA, -CR₈R'₈- (CH₂) ₁-C (= O) -XA or -C (= O) -O-CH₂-C (= CH₂) -R₁₀; and
in case E₁ is a group of formula If wherein none of R₂ and R₁₄ is hydrogen, R₁ additionally comprises -A and -CH₂-CH (OH) -CH₂-XA;
R₂, independently of one another, is H, C₁-C₁₂-alkyl, C₅-C₁₂-cycloalkyl, C₃-C₆-alkenyl, halogen, phenyl or trifluoromethyl;
R₂ ', independently of one another, C₁-C₁₈-alkoxy, C₂-C₁₈-alkenoxy, -OH or -O-COR₁₂; R₃ and R₃ ', independently of one another, H, -OH, -OR₁, -OR₁₃₁, C₁-C₁₈-alkyl, C₃-C₁₈-alkenyl, C₆-C₁₂-cycloalkyl, halogen, trifluoromethyl, phenyl, phenyl-C₁-C₄-alkyl , -CN, C₁-C₁₈-alkyl-S (= O) _t - or phenyl-S (= O) _t -;
R₄, R₄ 'and R₄'', independently of one another, H, C₁-C₁₈-alkyl, C₃-C₆-alkenyl, -OR₁₃₁, halogen, trifluoromethyl, phenyl, phenyl-C₁-C₄-alkyl, having one to three radicals C₁- C₄-alkyl-substituted phenyl-C₁-C₄-alkyl, -CN, C₁-C₁₈-alkyl-S (= O) _t - or phenyl-S (= O) _t -;
R₅ is H, -CH₂-COOR₁₃, C₁-C₄-alkyl or -CN;
R₆ is H, -COOR₁₃, C₁-C₁₇-alkyl or phenyl;
R₇ is C₁-C₁₈ alkyl; C₅-C₁₂ cycloalkyl; C₃-C₁₈ alkenyl; phenyl; with one to three radicals C₁-C₈-alkyl, C₁-C₈-alkoxy, C₃-C₈-alkenoxy, halogen or trifluoromethyl-substituted phenyl; Phenyl-C₁-C₄-alkyl; interrupted by one or more -O- interrupted C₃-C₅₀-alkyl;
1-adamantyl; 2-adamantyl; norbornyl; Norbornane-2-methyl; -C (= O) -R₁₂; -A;
R₈ and R₈ ', independently of one another, H, C₁-C₁₈-alkyl, phenyl, phenyl-C₁-C₄-alkyl, or with 1-3 C₁-C₈-alkyl, C₁-C₈-alkoxy, C₃-C₈-alkenoxy, halogen CF₃ substituted phenyl;
R₉ is C₁-C₁₈ alkyl, phenyl or phenyl-C₁-C₄ alkyl;
R₁₀ is H or -CH₃;
R₁₁ and R₁₁ 'are independently C₁-C₄ alkyl or phenyl or phenyl substituted with one to three C₁-C₈ alkyl, C₁-C₈ alkoxy, C₃-C₈ alkenoxy, halogen or trifluoromethyl;
R₁₂H, C₁-C₁₈-alkyl, phenyl, phenyl C₁-C₄-alkyl, C₅-C₁₂-cycloalkyl, C₁-C₁₂-alkoxy, phenoxy, norbornan-2-yl, 5-norbornen-2-yl, 1-adamantyl,
R-₃ is H, C₁-C₁₈ alkyl, C₃-C₁₈ alkenyl, phenyl, C₅-C₁₂ cycloalkyl, C₃-C₅₀ alkyl interrupted by one or more -O-; with one to three radicals C₁-C₈-alkyl, C₁-C₈-alkoxy,
C₃-C₈ alkenoxy, halogen or trifluoromethyl substituted phenyl; Phenyl-C₁-C₄-alkyl, 2-adamantyl; Norbornyl, norbornane-2-methyl;
R₁₄ and R₁₅, independently of one another, H, C₁-C₁₈-alkyl, C₃-C₁₈-alkenyl, C₆-C₁₂-cycloalkyl, halogen, CF₃, phenyl, phenyl-C₁-C₄-alkyl, CN, C₁-C₁₈-alkyl-S (= O) _t - or phenyl-S (= O) _t - or -OR₁₃₁;
R₁₃₁ C₁-C₁₈ alkyl; C₁-C₁₈-alkyl which is substituted by OH, C₁-C₁₈-alkoxy, C₅-C₁₂-cycloalkoxy, C₃-C₆-alkenyloxy, halogen, -COOR₁₃, -CONH₂, -COHNR₁₃₂, -CON (R₁₃₂) (R₁₃₃) , -NHCOR₁₂, CN, -OCOR₁₂, phenoxy, and / or by C₁-C₁₈-alkyl, C₁-C₁₈-alkoxy or halogen-substituted phenoxy; C₃-C₁₈ alkenyl; C₆-C₁₂ cycloalkyl;
C₆-C₁₂-cycloalkyl substituted by C₁-C₄alkyl and / or -OCOR₁₂; interrupted by one or more -O- interrupted C₃-C₅₀-alkyl which is unsubstituted or substituted by OH or O-CO-R₁₂; phenyl; Phenyl-C₁-C₄-alkyl; -COR₁₂; -SO₂R₁₂;
R₁₃₂ and R₁₃₃, independently, C₁-C₁₂ alkyl, C₃-C₁₂ alkoxyalkyl, C₄-C₁₆ dialkylaminoalkyl, C₅-C₁₂ cycloalkyl; or
R₁₃₂ and R₁₃₃ together C₃-C₉-alkylene, C₃-C₉-oxaalkylene or -Azaalkylen;
X is -NR₈-, -O-, NH- (C _n H _2n ) -NH- or O- (C _k H _2k ) -NH-;
k is a number 2-4;
l is a number 0-19;
m is a number 2-8;
n is a number 0-4;
p is a number 0-10;
q is a number 1-8;
r is a number 0-18; and
t is a number 0, 1 or 2. 6. A polymeric compound according to claim 5 obtainable by addition polymerization of at least one compound of formula (Ih) or at least one compound of formula (Ih) and at least one further ethylenically unsaturated compound wherein the radicals
A is -C (= O) -CR₅ = CH-R₆;
R₁ independently of one another, -CH₂-CH (OA) -CH₂-O-R₇, -CHR₈- (CH₂) ₁-OA,
-CH₂-CH (OA) -R₉, -CH₂-CH (OH) -CH₂-OA, -CH₂-C (= CH₂) -R₁₀, - (CH₂) _p -SiR₁₁R₁₁'-CH = CH₂, -C (= O) - (CH₂) _q -CH = CH₂, -CHR₈- (CH₂) _r -C ( = O) -O-CH₂-CH (OH) -CH₂-OA or
-C (= O) -O-CH₂-C (= CH₂) -R₁₀;
R₂ and R₂ 'are independently H, -OH, -OA, C₁-C₁₂ alkyl, cyclohexyl, C₃-C₆ alkenyl, C₁-C₁₈ alkoxy, C₂-C₁₈ alkenoxy, halogen, phenyl or trifluoromethyl;
R₃ and R₃ ', independently, H, -OH, -OA, -OR₁, C₁-C₁₂ alkyl, cyclohexyl, C₃-C₆ alkenyl, C₁-C₁₈ alkoxy, C₃-C₁₈ alkenoxy, halogen, trifluoromethyl, phenyl , Phenyloxy, phenyl-C₁-C₄-alkyl, phenyl-C₁-C₄-alkoxy, -CN, C₁-C₁₈-alkyl-S (= O) _t - or
Phenyl-S (= O) _t -;
R₄, R₄ 'and R₄'', independently of one another, H, C₁-C₁₂-alkyl, C₃-C₆-alkenyl, C₁-C₁₈-alkoxy, C₃-C₁₈-alkenoxy, halogen, trifluoromethyl, phenyl, phenyloxy, phenyl-C₁- C₄-alkyl, phenyl-C₁-C₄-alkyl substituted with one to three radicals C₁-C₄-alkyl, phenyl-C₁-C₄-alkoxy, -CN, C₁-C₁₈-alkyl-S (= O) _t - or phenyl- S (= O) _t -;
R₅ is H, -CH₂-COOR₁₃, C₁-C₄-alkyl or -CN;
R₆ is H, -COOR₁₃, C₁-C₁₇-alkyl or phenyl;
R₇ is C₁-C₁₈-alkyl, cyclohexyl, C₃-C₁₈-alkenyl, phenyl, substituted with one to three radicals C₁-C₈-alkyl, C₁-C₈-alkoxy, C₃-C₈-alkenoxy, halogen or trifluoromethyl
Phenyl, phenyl-C₁-C₄-alkyl, or -C (= O) -R₁₂;
R₈ is H or C₁-C₁₈ alkyl;
R₉ is C₁-C₁₈ alkyl, phenyl or phenyl-C₁-C₄ alkyl;
R₁₀ is H or -CH₃;
R₁₁ and R₁₁ 'are independently C₁-C₄ alkyl or phenyl or phenyl substituted with one to three C₁-C₈ alkyl, C₁-C₈ alkoxy, C₃-C₈ alkenoxy, halogen or trifluoromethyl;
R₁₂ is C₁-C₁₈ alkyl, C₂-C₁₈ alkenyl or phenyl;
R₁₃ is H, C₁-C₁₈ alkyl, C₃-C₁₈ alkenyl or phenyl;
l is a number 0-19;
p is a number 0-10;
q is a number 1-8;
r is a number 0-18; and
t is a number 0, 1 or 2. 7. A polymeric compound according to claim 5, wherein the radicals R₁, independently of one another, are -CH₂-CH (XA) -CH₂-O-R₇, -CR₈R₈ '- (CH₂) ₁-XA, -CH₂-CH (OA) -R₉, or
-CHR₈- (CH₂) _r -C (= O) -O-CH₂-CH (OH) -CH₂-OA;
R₂ is H, C₁-C₄ alkyl, C₃ alkenyl, F, Cl or phenyl;
R₂ 'C₁-C₄ alkoxy, C₃ alkenoxy, -OA, -O-COR₁₂ or -OH;
R₃ and R₃ 'are independently H, -OH, -OR₁, -OR₁₃₁, C₁-C₄alkyl, cyclohexyl, C₃-alkenyl, F, Cl, trifluoromethyl, phenyl, benzyl or -CN;
R₄ 'and R₄'', independently of one another, H, C₁-C₄-alkyl, C₃-alkenyl, C₁-C₄-alkoxy, C₃-alkenoxy, F, Cl, trifluoromethyl, phenyl, phenyl-C₁-C₃-alkyl or -CN ;
R₅ is H or -CH₃;
R₆ is H, -COOR₁₃, -CH₃ or phenyl;
R₇ is C₁-C₈-alkyl, cyclohexyl, C₃-C₈-alkenyl, phenyl, substituted with one to three radicals C₁-C₄-alkyl or C₁-C₄-alkoxy-substituted phenyl; or benzyl;
R₈ and R₈ ', independently of one another, are H or C₁-C₁₈-alkyl;
R₉ is C₁-C₁₀ alkyl, phenyl or benzyl;
R₁₂H, C₁-C₁₈-alkyl, phenyl, phenyl-C₁-C₄-alkyl or cyclohexyl;
R₁₃ is C₁-C₄alkyl, C₃-alkenyl, cyclohexyl, phenyl-C₁-C₄alkyl or phenyl;
R₄, R₁₄ and R₁₅, independently, H, F, Cl, C₁-C₄-alkoxy, CF₃, phenyl, CN or
C₁ to C₈ alkyl;
R₁₃₁ C₁-C₁₈ alkyl; C₃-C₁₈alkyl which is substituted by OH, C₁-C₁₈alkoxy, C₅-C₁₂-cycloalkoxy, -COOR₁₃, -CONH₂, -COHNR₁₃₂, -CON (R₁₃₂) (R₁₃₃), -NHCOR₁₂, CN, -OCOR₁₂ and / or phenoxy; C₃ alkenyl; C₆-C₁₂ cycloalkyl; interrupted by one or more -O- interrupted C₃-C₅₀-alkyl which is unsubstituted or substituted by OH or O-COR₁₂; phenyl; Phenyl-C₁-C₄-alkyl; -COR₁₂; -SO₂R₁₂;
X is -O- or -NR₈-;
l is a number 1-19; and
r is a number 0-10. 8. A polymeric compound according to claim 5, wherein the radicals A -C (= O) -CR₅ = CH-R₆;
R₁ independently of one another, -CH₂-CH (OA) -CH₂-O-R₇, -CH₂-CH (OA) -R₉, or -CHR₈- (CH₂) ₁-OA;
R₂ is H, CH₃, OCH₃, C₃-alkenoxy or Cl;
R₂'-OH;
R₃ is H, -CH₃, C₁-C₄-alkoxy, C₃-alkenoxy, F, Cl, phenyl, benzyloxy or -CN;
R₃'-OR₁ or -OR₁₃₁;
R₄, R₁₄ and R₁₅, independently, H, F, Cl, phenyl, CN, OCH₃ or CH₃;
R₄ 'and R₄'', independently of one another, H, -CH₃, C₃-alkenyl, -OCH₃, C₃-alkenoxy, F, Cl,
Phenyl-C₃-alkyl or -CN;
R₅ is H or -CH₃;
R₆ is H or -CH₃;
R₇ is C₁-C₈alkyl, cyclopentyl, cyclohexyl, C₃-alkenyl, phenyl or benzyl;
R₈ is H or C₁-C₁₈ alkyl;
R₉ is C₁-C₁₀ alkyl or phenyl;
R₁₂ is C₁-C₁₈ alkyl, phenyl or cyclohexyl;
R₁₃₁ C₃-C₁₈ alkyl or C₃-C₁₈ alkyl which is substituted by C₁-C₁₈ alkoxy, OH, phenoxy, -NHCOR₁₂ and / or -OCOR₁₂; and
l is a number 1-19. 9. A polymeric compound according to claim 5, wherein the radicals A -C (= O) -CR₅ = CH-R₆;
R₁ independently of one another, -CH₂-CH (OA) -CH₂-O-R₇, -CH₂-CH (OA) -R₉, or -CH₂- (CH₂) ₁-OA;
R₂ is H or CH₃;
R₂'-OH;
R₃ is H, -CH₃, Cl or phenyl;
R₃'-OR₁ or -OR₁₃₁;
R₄ is H or CH₃;
R₄ ', R₄'', R₁₄ and R₁₅ hydrogen;
R₅ is H or -CH₃;
R₆ H;
R₇ is C₁-C₈ alkyl;
R₉ is C₁-C₁₀ alkyl;
R₁₂ C₁-C₈ alkyl;
R₁₃₁ C₃-C₁₈ alkyl or C₃-C₁₈ alkyl which is substituted by -OCOR₁₂; and
l is a number 1-10. 10. A polymeric compound according to claim 5 obtainable by copolymerization at least one compound of formula (Id), according to claim 5 and at least one further comonomers, wherein the further comonomer is selected from acrylic acid, Methacrylic acid, acrylates, methacrylates, acrylamides, methacrylamides, vinyl ethers, Styrene, styrene derivatives, vinylpyridines, acrylonitrile, methacrylonitrile, vinylpyrrolidone, Derivatives of vinylpyrrolidone, as well as ethylenically unsaturated derivatives of steric hindered amines, 2- (2'-hydroxyphenyl) benzotriazoles, 2-hydroxy-benzophenones or hindered phenols. 11. A polymeric compound according to claim 10, wherein another comonomer of one of the formulas (II) - (VII) (II) R₁₈-CH = C (R₁₇) -C (= O) -X'-R₂₀, wherein X 'is -O - or -NR₁₉-;
R₁₇ is H, C₁-C₄ alkyl, -CH₂-COOR₂₁, -Cl or -CN;
R₁₈ H, -COOR₂₁ or -CH₃;
R₁₉ H, C₁-C₈-alkyl, C₄-C₁₂-cycloalkyl, by -N (R _X ) ₂ substituted C₁-C₄-alkyl, -S (= O) -R _X , -C (CH₃) ₂-CH₂- C (= O) -CH₃, -C (CH₃) ₂-CH₂-SO₃M, - (CH₂) s-SO₃M or R₂₀H; C₁-C₁₈ alkyl; C₃-C₁₈ alkenyl; interrupted by one or more O atoms C₂-C₃₀-alkyl which may be substituted by OH; or - (CH₂) _s -SO₃M; -CH₂F; -CH₂Cl; -CH₂CN; -CH₂CH₂Cl;
-CH₂CH₂CN; -CH₂CH₂-COOR _X ; C₇-C₁₁ phenylalkyl; naphthyl; by -N (R _X ) ₂ substituted C₁-C₄-alkyl; adamantyl; C₆-C₁₂ cycloalkyl;
R₂₁ is H, C₁-C₁₈ alkyl, phenyl or C₃-C₁₈ alkenyl;
R _{X is} C₁-C₄ alkyl or phenyl;
R _{Y is} H, C₁-C₁₂-alkyl, phenyl, -CO-OR _X , -CN, -F, -Cl;
MH or an alkali metal; and
s is a number between 1 and 5;
(III) R₂₂-C (= O) -O-CH = CH₂,
wherein R₂₂ is C₁-C₁₉ alkyl or phenyl;
(IIIa) _R22a -O-CH = CH₂,
wherein R _{22a is} C₁-C₁₈ alkyl; wherein R₂₃ is H or -CH₃;
R₂₄ is H, -CR₂₃ = CH₂, -C (O) -phenyl or -SO₃M; and
MH or an alkali metal means; wherein R₂₅ is H or -CH₃;
(VI) CH₂ = CR₂₆-R₂₇,
wherein R₂₆ is H, -F, -Cl or -CH₃ and R₂₇-Cl, -Br, - F or -CN; equivalent. 12. A polymeric compound according to claim 11 obtainable by copolymerization of at least one compound of the formula (Id), and at least one further comonomer of one of the formulas (II) - (IV) or (VII) according to claim 11, wherein
R₁₇ is H or -CH₃;
R₁₈ is H or -CH₃;
R₁₉ is H, C₁-C₄ alkyl, -C (CH₃) ₂-CH₂-SO₃M or - (CH₂) _s -SO₃M;
R₂₀ H, C₁-C₈-alkyl or interrupted by one or more O atoms C₂-C₂₀-alkyl;
R₂₂ -CH₃;
R _{22a is} C₁-C₄ alkyl;
R₂₃ and R₂₄ H;
MH, Li, Na or K.
X is -O- or -NR₁₉-; and
s is the number 2 or 3. 13. Process for the incorporation of 2-hydroxyphenyltriazines into organic polymers, characterized in that a compound of the formula (I) according to Claim 1 either in the preparation of the polymer by copolymerization, Copoly condensation or copolyaddition or with a polymer which is suitable contains functional groups, reacts.   14. Organic polymer obtainable according to claim 13, characterized in that it 0.05 to 50 wt .-% of the compound of formula (I). 15. An organic material containing a compound of formula (I) according to claim 1 or a polymeric compound according to claim 5. 16. Organic material according to claim 15, wherein the organic material is a is organic polymer. 17. Organic material according to claim 15, wherein the organic material is a Binder for a coating agent is. 18. Method for stabilizing organic material against the harmful Influence of light, oxygen and / or heat, characterized in that one as stabilizer a compound of formula (I) according to claim 1 or a polymeric Compound according to claim 5 added. 19. Use of a compound of formula (I) according to claim 1 or one A polymeric compound according to claim 5 for stabilizing organic material against the damaging influence of light, oxygen and / or heat.